Phenol → (4-Fluoro-2-nitro-5-phenoxy-phenyl)-methanol

HRID 252467Notes

Reaction equation

[F:1][C:2]1[C:7](F)=[CH:6][C:5]([CH2:9][OH:10])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[F:1][C:2]1[C:7]([O:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:6][C:5]([CH2:9][OH:10])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (4,5-difluoro-2-nitrophenyl)methanol (950 mg, 5 mmol) in DMF (15 mL) were added potassium carbonate (1.23 g, 10 mmol) and phenol (520 mg, 5.5 mmol). The resulting mixture was stirred at 50° C. overnight, cooled to room temperature, filtered, washed with ethyl acetate (2×20 mL), and concentrated. The resulting crude mixture was purified by chromatography (silica gel, 30-70% ethyl acetate in heptane) to yield a slightly yellow solid.

Workup

temperaturecooled to room temperature
filtrationfiltered
washwashed with ethyl acetate (2×20 mL)
concentrationconcentrated
customThe resulting crude mixture was purified by chromatography (silica gel, 30-70% ethyl acetate in heptane)
customto yield a slightly yellow solid

Sources & evidence

ORD record: ord-93fbf8e7d66c4f148b1b5395514f427c
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868022B2

Reaction notes

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