4-Bromo-1,2-difluorobenzene → HCID 178495610, compound

HRID 1080593Notes

Reaction equation

HRID 1080593 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([F:9])[CH:3]=1.[Mg].[CH3:11][O:12][CH2:13][CH2:14][CH2:15][Si@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][C@H:24]2[CH2:29][CH2:28][C@H:27]([C:30]3[CH:35]=[CH:34][C:33](Br)=[CH:32][CH:31]=3)[CH2:26][CH2:25]2)[CH2:18][CH2:17]1>C1COCC1>[CH3:11][O:12][CH2:13][CH2:14][CH2:15][Si@H:16]1[CH2:17][CH2:18][C@H:19]([CH2:22][CH2:23][C@H:24]2[CH2:29][CH2:28][C@H:27]([C:30]3[CH:35]=[CH:34][C:33]([C:2]4[CH:7]=[CH:6][C:5]([F:8])=[C:4]([F:9])[CH:3]=4)=[CH:32][CH:31]=3)[CH2:26][CH2:25]2)[CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 676754-Bromo-1,2-difluorobenzeneHCID 5462224MagnesiumHCID 178495609HCID 178495609, compound

Product 1

HCID 178495610HCID 178495610, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

19.3 g (0.1 mol) of 1-bromo-3,4-difluorobenzene was dripped into a mixture of 2.5 g (0.11 mol) of magnesium and 300 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 500 ml THF solution of 0.5 g of tetrakis triphenylphosphine palladium and 43.8 g (0.1 mol) of 4-(trans-4-(2-(trans-4-(3-methoxypropyl)-4-silacyclohexyl)ethyl)cyclohexyl)phenyl bromide. After a conventional after treatment, purification was conducted by means of chromatography to obtain 28.9 g (yield 61.3%) of 4-(trans-4-(2-(trans-4-(3-methoxypropyl)-4-silacyclohexyl)ethyl)cyclohexyl)-3',4'-difluorobiphenyl was obtained.

Workup

  1. customto obtain a Grignard's reagent
  2. customAfter a conventional after treatment, purification

Sources & evidence

ORD record
ord-99d600a020a94300992eda134b991735
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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