Diglyme → 1-(2,2,2-Trifluoro-1-trifluoromethyl-ethyl)-4-vinyl-benzene

HRID 642852Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.CO[CH2:19][CH2:20]OCCOC.[Li+].[Cl-].C(C([Sn])=C(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[F:10][C:9]([F:12])([F:11])[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:19]=[CH2:20])=[CH:3][CH:4]=1)[C:13]([F:16])([F:15])[F:14]

Participants

Conditions

Temperature: 80 °C

Procedure

Crude 1-bromo-4-(2,2,2-trifluoro-1-trifluoromethyl-ethyl)-benzene, (approximately 100 mg of starting material, contaminated with diglyme) was dissolved in toluene (3 ml) in a sealed tub under a nitrogen atmosphere. Tetrakispalladium (15 mg, 0.013 mmol) and LiCl (42 mg, 1 mmol) were added, followed by the addition of tributylvinyltin (155 mg, 0.49 mmol).The reaction mixture was heated to 80° C. for 18 h, and then purified by silica gel column chromatography (100% hexane -2% ethyl acetate/hexane) to yield the title product, whose volatility made yield calculations impossible. 1H NMR (CDCl3) δ=7.49 (d, J=8.4 Hz, 2H), 7.40 (d, J=8.4 Hz, 2H), 6.71 (dd, J=10.9, 17.6 Hz, 1H), 5.82 (d, J=17.7, 1H), 5.33 (d, J=10.9 Hz, 1H), 4.06 (septet, JH,F=8.3 Hz,1H).

Workup

custompurified by silica gel column chromatography (100% hexane -2% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-465f62a82fee4a76ace298c902222b88
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696210B2

Reaction notes

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