Tetrahydrofuran → 1-Chloro-2-(trifluoromethyl)-4-(4-vinylphenoxy)benzene

HRID 705875Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)=[CH:6][C:5]=1[C:19]([F:22])([F:21])[F:20].[CH2:23]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[CH2:23])=[CH:13][CH:12]=2)=[CH:6][C:5]=1[C:19]([F:22])([F:21])[F:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyltriphenylphosphonium bromide (5.99 g, 16.76 mmol) and NaH (1.397 g, 34.9 mmol) in THF (50 mL) was added a solution of 4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}benzaldehyde (4.2 g, 13.97 mmol) in THF (50 mL) under nitrogen at 0° C. The reaction mixture was stirred at 0° C. for 0.5 h, then at room temperature overnight. Purification via flash chromatography then afforded the title compound (3.6 g, 12.05 mmol, 86% yield).

Workup

customat room temperature
customovernight
customPurification via flash chromatography

Sources & evidence

ORD record: ord-4c78b6d5d81b488c8675e65ad5cebb73
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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