Triethylamine → Ethyl [4-(trifluoromethyl)phenyl]-{4-(isopropoxy)-3-vinylphenyl}phosphinate

HRID 420099Notes

Reaction equation

[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([PH:9](=[O:13])[O:10][CH2:11][CH3:12])=[CH:5][CH:4]=1.Br[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:26])[CH3:25])=[C:19]([CH:27]=[CH2:28])[CH:18]=1.C(N(CC)CC)C>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:15][C:2]([F:14])([F:1])[C:3]1[CH:4]=[CH:5][C:6]([P:9]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:25])[CH3:26])=[C:19]([CH:27]=[CH2:28])[CH:18]=2)(=[O:13])[O:10][CH2:11][CH3:12])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a degassed solution of ethyl 4-(trifluoromethyl)-phenylphosphinate (1.00 g, 4.20 mmol) and 4-bromo-1-isopropoxy-2-vinylbenzene (921 mg, 3.81 mmol) in DMF (40 mL) were added the triethylamine (1.1 mL, 7.62 mmol) and tris(dibenzylideneacetone)dipalladium (698 mg, 0.762 mmol). The mixture was warmed at 70° C. overnight. The volatiles were removed in vacuo and the residue was purified by column chromatography using 5 to 100% ethyl acetate in petroleum ether to afford compound BA1 (130 mg) as a dark green oil in 8.6% yield.

Workup

customThe volatiles were removed in vacuo
customthe residue was purified by column chromatography
customto afford compound BA1 (130 mg) as a dark green oil in 8.6% yield

Sources & evidence

ORD record: ord-2000c9b87754483fa9fbdbc46d642bf9
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093379B2

Reaction notes

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