4-(4-Chloro-3-trifluoromethyl-phenoxy)-3-fluoro-benzaldehyde → 4-Chloro-3-(trifluoromethyl)phenyl 4-ethenyl-2-fluorophenyl ether

HRID 705834Notes

Reaction equation

HRID 705834 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:21]=CC(C=O)=[CH:16][C:15]=2[F:22])=[CH:9][C:8]=1[C:23]([F:26])([F:25])[F:24]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH:3]([C:2]1[CH:1]=[CH:21][C:14]([O:13][C:10]2[CH:11]=[CH:12][C:7]([Cl:6])=[C:8]([C:23]([F:25])([F:26])[F:24])[CH:9]=2)=[C:15]([F:22])[CH:16]=1)=[CH2:4]

Participants

5

Reactant 2

HCID 866661984-(4-Chloro-3-trifluoromethyl-phenoxy)-3-fluoro-benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 677746594-Chloro-3-(trifluoromethyl)phenyl 4-ethenyl-2-fluorophenyl etherYield 80.5%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyltriphenylphosphonium bromide (6.73 g, 18.83 mmol) in anhydrous THF (20 mL) was added dropwise n-butyllithium (11.77 mL, 18.83 mmol) under −78° C. over 30 min. It was stirred for 1 h, then was added by 4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3-fluorobenzaldehyde (5.0 g, 15.69 mmol). It was warmed slowly to room temperature and stirred for overnight at room temperature. Purification via a flash column chromatography then afforded the title compound (4.0 g, 80% yield). LCMS: rt=5.7 min, [M+H+]=316

Workup

  1. stirringstirred for overnight at room temperature
  2. customPurification via a flash column chromatography

Sources & evidence

ORD record
ord-b05b4b10b9fb4568a375e3490bcc24ca
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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