3-Chloro-2-trifluoromethylbenzoic acid → HCID 118162167, compound

HRID 1749488Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:11]([F:14])([F:13])[F:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6]>C1COCC1>[Cl:1][C:2]1[C:3]([C:11]([F:12])([F:13])[F:14])=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 3-chloro-2-(trifluoromethyl)benzoic acid (0.15 g, 0.668 mmol) in THF (5 mL) was added dropwise a solution of borane dimethyl sulfide complex in THF (2 M, 0.70 mL, 1.40 mmol) at 0° C. to 5° C. The resulting solution was heated at 75° C. for 2 h under nitrogen atmosphere. The reaction was quenched with MeOH (1 mL) at 0° C. and concentrated under vacuum to give the crude title product (0.12 g). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.66-7.64 (m, 1H), 7.48-7.44 (m, 2H), 4.90 (d, J=2.0 Hz, 2H), 3.70 (t, J=2.0 Hz, 1H).

Workup

customThe reaction was quenched with MeOH (1 mL) at 0° C.
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-afad6e60ea7640f6b33cbf75e9fe556e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156798B2

Reaction notes

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