1-Bromo-3,5-bis(trifluoromethyl)benzene → HCID 86632301, compound

HRID 643597Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:16]([NH:19][C:20](=[CH2:25])[C:21]([O:23][CH3:24])=[O:22])(=[O:18])[CH3:17].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:16]([NH:19][C:20](=[CH:25][C:5]1[CH:4]=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=1)[C:21]([O:23][CH3:24])=[O:22])(=[O:18])[CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

Under a nitrogen atmosphere 50.0 g (171 mmol) 3,5-bis-(trifluoromethyl)-bromobenzene, 25.0 g (171 mmol) methyl 2-acetylamino-acrylate in 475 mL triethylamine and 250 mL acetonitrile were combined with 3.9 g (12.4 mmol) tri-o-tolyl-phosphane and 2.8 g (12.5 mmol) Pd(OAc)2 and stirred for 18 h at 80° C. After the reaction had ended the reaction mixture was evaporated down i. vac. to approx. 200 mL, combined with 400 mL EtOAc and 400 mL water, the precipitate was suction filtered and the phases were separated. The organic phase was dried over Na2SO4, combined with activated charcoal, filtered and evaporated to dryness. The residue was stirred with DIPE, suction filtered and dried i. vac.

Workup

customwas evaporated down i
filtrationfiltered
customthe phases were separated
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
customevaporated to dryness
stirringThe residue was stirred with DIPE, suction
filtrationfiltered
customdried i

Sources & evidence

ORD record: ord-d39ecf55f16e4e64bf5eb4f56bd2ace3
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700598B2

Reaction notes

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