Methanol → HCID 118046800, compound

HRID 63878Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[C:20]([F:24])=[C:19]([Cl:25])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:26].[C:27]([O-:30])(=[O:29])C.[Na+].[CH3:32]O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:25][C:19]1[CH:18]=[C:17]([C:11]2([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:27]([O:30][CH3:32])=[O:29])=[C:3]([CH3:26])[CH:4]=3)[CH2:12]2)[CH:22]=[C:21]([Cl:23])[C:20]=1[F:24]

Participants

Conditions

Temperature: 110 °C

Procedure

Into a 30-mL pressure tank reactor (20 atm), was placed methanol (10 mL), 3-(4-bromo-3-methylphenyl)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole (80 mg, 0.17 mmol, 1.00 equiv), sodium acetate (41 mg, 0.50 mmol, 3.00 equiv), Pd(dppf)Cl2 (12 mg, 0.02 mmol, 0.10 equiv), CO (20 atm). The resulting solution was stirred overnight at 110° C. in an oil bath. The reaction mixture was cooled. The residue was purified by Prep-TLC (EtOAc:PE=10:1). This resulted in 60 mg (78%) of methyl 4-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoate as colorless oil.

Workup

customInto a 30-mL pressure tank reactor (20 atm), was placed
temperatureThe reaction mixture was cooled
customThe residue was purified by Prep-TLC (EtOAc:PE=10:1)
customThis resulted in 60 mg (78%) of methyl 4-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoate as colorless oil

Sources & evidence

ORD record: ord-08c948a789b84a4ba92f40f0ecfa1a4d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447084B2

Reaction notes

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