4-Fluoro-3-(trifluoromethyl)benzoic acid → HCID 59384377, compound

HRID 2357070Notes

Reaction equation

HRID 2357070 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]>C(#N)C.O>[CH2:6]([O:7][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH2:4]

Participants

3

Reactant 1

HCID 5222684-Fluoro-3-(trifluoromethyl)benzoic acid

Product 1

HCID 59384377HCID 59384377, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared from 4-fluoro-3-(trifluoromethyl)benzoic acid (1a) in >99% (5.65 g) yield. HPLC retention time on a C8(2) column (30×3.00 mm, 3 i) was 2.53 min with gradient 20-98% acetonitrile-H2O (0.1% TFA) in 4.0 min as mobile phase. 1H NMR (400 MHz, DMSO-d6) δ 13.10 (br s, 1H), 8.15 (dd, 1H, J=8.8 Hz, J=2.4 Hz), 8.08 (d, 1H, J=2.4 Hz), 7.35 (d, 1H, J=8.8 Hz), 5.95-6.80 (m, 1H), 5.38-5.45 (m, 1H), 5.26-5.32 (m, 1H), 4.77-4.82 (m, 2H).

Workup

  1. customyield

Sources & evidence

ORD record
ord-325068928e964fe18893c78f14a85567
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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