3-(Trifluoromethyl)phenol → 3-(Trifluoromethyl)-4-(3-(trifluoromethyl)phenoxy)benzaldehyde

HRID 474627Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[F:14][C:15]([F:24])([F:23])[C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[F:11][C:10]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[O:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:15]([F:14])([F:23])[F:24])[CH:17]=1)[CH:6]=[O:7]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-fluoro-3-(trifluoromethyl)benzaldehyde (0.355 mL, 2.60 mmol), 3-(trifluoromethyl)phenol (0.289 mL, 2.60 mmol) and K2CO3 (1079 mg, 7.81 mmol) were in DMSO (10 mL) was heated at 100° C. overnight. Purification via reverse phase flash chromatography afforded the title compound (989 mg, 2.368 mmol, 91.0% yield). LCMS: rt=3.84 min, [M+H+]=335

Workup

customPurification via reverse phase flash chromatography

Sources & evidence

ORD record: ord-67c19772d2b045d8ac7321929bfb6e2b
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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