Water → (3-Bromo-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methanol

HRID 1666457Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([CH2:8][OH:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=1.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([O:10][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=2)[CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3-bromo-5-(hydroxymethyl)phenol (3.0 g, 14.77 mmol) in DMF (15 mL) under a N2 atmosphere was added potassium carbonate (4.08 g, 29.55 mmol) and the mixture was stirred for 20 min. 2-Chloro-5-(trifluoromethyl)pyridine (2.68 g, 14.77 mmol) was added at RT and then the reaction was refluxed at 110° C. overnight. The reaction mixture was cooled and water was added. The mixture was extracted with ethyl acetate three times. The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness to give the title compound (5.5 g) which was used in the next step without purification. 1H NMR (500 MHz, CDCl3): δ 8.44 (s, 1H), 7.92 (d, J=8.5 Hz, 1H), 7.41 (s, 1H), 7.24 (s, 1H), 7.19 (s, 1H), 7.04 (d, J=9 Hz, 1H), 4.71 (s, 2H); m/z (348, 349.9, M+H+).

Workup

temperatureThe reaction mixture was cooled
extractionThe mixture was extracted with ethyl acetate three times
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-5e179b8f8f2449d0a2e77dbd6353f578
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044052B2

Reaction notes

Loading…