2-Fluorobenzoic acid → HCID 86594893, compound

HRID 488518Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13](N)=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].[Li+].C[Si]([N-:26][Si](C)(C)C)(C)C.F[C:32]1[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=1[C:34]([OH:36])=[O:35]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:40]3[C:32]([NH2:26])=[C:33]([CH:37]=[CH:38][CH:39]=3)[C:34]([OH:36])=[O:35])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18]

Participants

Conditions

Temperature: -78 °C

Procedure

To a cold solution of 4-[2-(4-chloro-3-trifluoromethylphenyl)ethyl]-benzenamine (4.33 g, 14.45 mmol) in THF (50 mL) at −78° C., was added LHMDS (43.35 mL, 43.35 mmol) (1M/THF) dropwise. Allowed the reaction mixture to stir for 10 minutes at −78° C. A solution of 2-fluorobenzoic acid (2.02 g, 14.45 mmol) in THF (50 mL) was added dropwise. The mixture was stirred for 2 hours at −78° C., then warmed to room temperature and let stir for additional 3 hours. The reaction mixture was concentrated in vacuo (40° C.) to remove the organic solvent. This residue was acidified to pH 3 with 3N HCl (aq.). This precipitate was collected by filtration, rinsed with 10% HCl (40 mL), and dried in vacuum for overnight to give as a pale solid, 4.3 g (10.24 mmol, 70%) of the desired product. mp 150-152° C.

Workup

stirringThe mixture was stirred for 2 hours at −78° C.
temperaturewarmed to room temperature
stirringlet stir for additional 3 hours
concentrationThe reaction mixture was concentrated in vacuo (40° C.)
customto remove the organic solvent
filtrationThis precipitate was collected by filtration
washrinsed with 10% HCl (40 mL)
customdried in vacuum for overnight

Sources & evidence

ORD record: ord-568eb4af4bc242808e47d2929d0f5fcb
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972287B1

Reaction notes

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