1412
P. Cyr, A. B. Charette
LETTER
(17) See the Supporting Information for more details.
(18) Song, H.; Tice, J. D.; Ismagilov, R. F. Angew. Chem. Int. Ed.
2003, 42, 767.
(19) (a) Hatekeyama, T.; Chen, D. L.; Ismagilov, R. F. J. Am.
Chem. Soc. 2006, 128, 2518. (b) Benali, O.; Deal, M.;
Farrant, E.; Tapolczay, D.; Wheeler, R. Org. Process Res.
Dev. 2008, 12, 1007.
(20) (a) Sarma, K. D.; Maitra, U. Tetrahedron 1998, 54, 4965.
(b) Galevskaya, T. P.; Moroz, A. A.; Myasnikova, R. N.;
Shvartsberg, M. S. J. Org. Chem. USSR (English
References
(1) (a) Rappoport, Z. The Chemistry of Phenols; Wiley-VCH:
Weinheim, 2003. (b) Tyman, J. H. P. Synthetic and Natural
Phenols; Elsevier: New York, 1996.
(2) (a) Hale, W. J.; Britton, E. C. Ind. Eng. Chem. 1928, 20, 114.
(b) Boudakian, M. M.; Eber, R. J.; Kuehlewind, W. E.;
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(3) Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L.
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Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem.
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Loria, N. L.; McDonald, R.; Stradiotto, M. Adv. Synth.
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(5) Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem.
Int. Ed. 2009, 48, 8725.
(6) Zhao, D.; Wu, N.; Zhang, S.; Xi, P.; Su, X.; Lan, J.; You, J.
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(7) (a) Paul, R.; Ali, M. A.; Punniyamurthy, T. Synthesis 2010,
4268. (b) Maurer, S.; Liu, W.; Zhang, X.; Jiang, Y.; Ma, D.
Synlett 2010, 976. (c) Chen, J.; Yuan, T.; Hao, W.; Cai, M.
Catal. Commun. 2011, 12, 1463. (d) Xu, H.; Liang, Y.; Cai,
Z.; Qi, H.; Yang, C.; Feng, Y. J. Org. Chem. 2011, 76, 2296.
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(8) For an example using microwave heating, see: Mehmood,
A.; Leadbeater, N. E. Catal. Commun. 2010, 12, 64.
(9) Mousseau, J. J.; Bull, J. A.; Charette, A. B. Angew. Chem.
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69, 1776. (b) Diemer, V.; Leroux, F. R.; Colobert, F. Eur. J.
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(22) Phenol Synthesis; General Procedure: A solution of the
aryl iodide (4.83 mmol) in a mixture of aq n-Bu4NOH (1.5
M, 19.3 mL) and DMSO (19.3 mL, for an overall 0.125 M
solution vs. aryl iodide) was prepared. The reaction solution
(37 mL) was injected by using direct injection mode and the
reagent stream was pumped into the 10-mL copper reactor
(1.0 mm i.d.) at the desired temperature for the needed
residence time, then 48 mL of the crude reaction solution
was collected, acidified to pH 1 with 2 M HCl. H2O (150
mL) was added and the mixture was extracted with Et2O
(3 × 150 mL). The combined organic layers were dried over
anhydrous MgSO4, filtered, and concentrated under vacuum.
The crude mixture was purified by flash chromatography
(CH2Cl2–hexanes gradient) to afford the desired product (see
the Supporting Information for more details).
(23) Benzyl-3-chlorophenyl Ether (3); Typical Procedure: A
first solution (A) of 1-chloro-3-iodobenzene (1b; 0.50 g,
2.10 mmol) in a mixture of aq n-Bu4NOH (1.5 M, 8.4 mL)
and DMSO (8.4 mL; for an overall 0.125 M solution vs. 1-
chloro-3-iodobenzene) was prepared. A second solution (B)
consisting of benzyl bromide (0.62 mL, 6.30 mmol) in
DMSO (8 mL) was prepared. Solution A was injected using
the direct injection mode and the reagent stream was pumped
into the first reactor (10 mL copper coil of 1.0 mm i.d.) at
165 °C. Then, solution B was injected by using the direct
injection mode and mixed in a T-mixer with solution A after
the latter had passed the first reactor. The mixture then
passed the second reactor (5 mL PFA coil of 1.0 mm i.d.) at
150 °C. 23 mL of the crude reaction solution was then
collected, diluted with H2O (100 mL) and extracted with
Et2O (3 × 100 mL). The combined organic layers were dried
over anhydrous MgSO4, filtered, and concentrated under
vacuum. The crude mixture was purified by flash
(11) He, Z.; Jamison, T. F. Angew. Chem. Int. Ed. 2014, 53, 3353.
(12) For some exceptions only using water, see: (a) Yang, D.; Fu,
H. Chem. Eur. J. 2010, 16, 2366. (b) Jing, L.; Wei, J.; Zhou,
L.; Huang, Z.; Li, Z.; Zhou, X. Chem. Commun. 2010, 46,
4767.
(13) Kormos, C. M.; Leadbeater, N. E. Tetrahedron 2006, 62,
4728.
(14) Bogdan, A. R.; Sach, N. Adv. Synth. Catal. 2009, 351, 849.
(15) Zhang, Y.; Jamison, T. F.; Patel, S.; Mainolfi, N. Org. Lett.
2011, 13, 280.
chromatography (CH2Cl2–hexanes, 0–30%) to afford 3 (385
mg, 84% yield) as a yellow solid (see the Supporting
Information for more details).
(16) Copper coil flow reactors are available from Vapourtec Ltd.,
Synlett 2014, 25, 1409–1412
© Georg Thieme Verlag Stuttgart · New York