1-Bromo-3,4,5-trifluorobenzene → HCID 178460939, compound

HRID 1080592Notes

Reaction equation

HRID 1080592 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([F:10])[CH:3]=1.[Mg].[CH2:12]([Si@H:15]1[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][C@H:23]2[CH2:28][CH2:27][C@H:26]([C:29]3[CH:34]=[CH:33][C:32](I)=[C:31]([F:36])[CH:30]=3)[CH2:25][CH2:24]2)[CH2:17][CH2:16]1)[CH2:13][CH3:14]>C1COCC1>[CH2:12]([Si@H:15]1[CH2:16][CH2:17][C@H:18]([CH2:21][CH2:22][C@H:23]2[CH2:28][CH2:27][C@H:26]([C:29]3[CH:34]=[CH:33][C:32]([C:2]4[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([F:10])[CH:3]=4)=[C:31]([F:36])[CH:30]=3)[CH2:25][CH2:24]2)[CH2:19][CH2:20]1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 5462224MagnesiumHCID 178460942HCID 178460942, compound

Product 1

HCID 178460939HCID 178460939, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

21.1 g (0.1 mol) of 1-bromo-3,4,5-trifluorobenzene 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 47.3 g (0.1 mol) of 4-(trans -4-(2-(trans-4-n-propyl-4-silacyclohexyl)ethyl)cyclohexyl) -2-fluorophenyl iodide. After a conventional after treatment, purification was conducted by means of chromatography to obtain 37.7 g (yield 79.1%) of 4-(trans-4-(2-(trans-4-n-propyl-4-silacyclohexyl)ethyl)cyclohexyl)-2,3',4',5'-tetrafluorobiphenyl was obtained.

Workup

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

Sources & evidence

ORD record
ord-8973441f40224211863bd09d644e5487
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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