Water → 2-(3-Bromophenoxy)-5-(trifluoromethyl)pyridine

HRID 1666484Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3-bromophenol (5 g, 27.54 mmol) and 2-chloro-5-(trifluoromethyl)pyridine (4.52 g, 26.16 mmol) in DMF (30 mL) was added K2CO3 and the mixture was refluxed at 110° C. overnight. Distilled water (30 mL) and diethyl ether (30 mL) were added and the mixture was stirred for 30 min. The ether layer was dried over Na2SO4 and concentrated to give pure pure title compound (8.0 g). 1H NMR (500 MHz, CDCl3): δ 7.0 (d, 1H, J=10 Hz), 7.1 (d, 1H, J=1.5 Hz), 7.2-7.3 (m, 2H), 7.4 (d, 1H, J=8 Hz), 7.9 (m, 1H), 8.4 (s, 1H).

Workup

dry with materialThe ether layer was dried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-569cf1d0650843c7b11f5a3d1ac0d837
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044052B2

Reaction notes

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