Dimethylformamide → 4-(4-n-Heptyl-4-phenyl-4-silacyclohexyl)-1-(2-methylbutyl)-2,6-difluorobenzene

HRID 2647

Reaction equation

FC(F)(F)S(O[C:7]1[C:12]([F:13])=[CH:11][C:10]([CH:14]2[CH2:19][CH2:18][Si:17]([CH2:26][CH2:27][CH2:28][CH2:29]CCC)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[CH:9][C:8]=1[F:33])(=O)=O.[Cl-].[Li+].CN(C)C=O>C1COCC1.[Cl-].[Zn+2].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:26]([Si:17]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:16][CH2:15][CH:14]([C:10]2[CH:11]=[C:12]([F:13])[C:7]([CH2:11][CH:10]([CH3:14])[CH2:9][CH3:8])=[C:8]([F:33])[CH:9]=2)[CH2:19][CH2:18]1)[CH2:27][CH2:28][CH2:29][CH2:21][CH2:20][CH3:25]

Participants

Conditions

Temperature: 50 °C

Procedure

3.0 g (20 mmols) of (S)-1-bromo-2-methylbutane was dropped in a mixture of 0.5 g (21 mmols) of magnesium and 50 ml of THF to obtain a Grignard reagent. This reagent was dropped in 20 ml of a THF solution of 2.8 g (20 mmols) of zinc chloride to obtain an organizing reagent. Subsequently, the solution was dropped in a mixture of 10.7 g (20 mmols) of (2,6-difluoro-4-(4-n-heptyl-4-phenyl-4-silacyclohexyl)phenyl) trifluoromethanesulfonate, 100 mg of tetrakis(triphenylphosphine)palladium (0), 500 mg of lithium chloride and 50 ml of N,N-dimethylformamide, and agitated at 50° C. for 8 hours. The reaction mixture was after-treated by a usual manner and purified through chromatography to obtain 6.4 g (yield: 70%) of 4-(4-n-heptyl-4-phenyl-4-silacyclohexyl)-1-(2-methylbutyl)-2,6-difluorobenzene.

Workup

customto obtain an organizing reagent
additionThe reaction mixture was after-treated by a usual manner
custompurified through chromatography

Sources & evidence

ORD record: ord-46318b77785946d0ac36cbc991b8c83d
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05730902

Linked notes

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