Magnesium → HCID 178460937, compound

HRID 1080584Notes

Reaction equation

HRID 1080584 reaction equation
Br[CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[C:11]([F:22])[CH:10]=2)[CH2:5][CH2:4]1.[Mg].Br[CH2:25][C@H:26]1[CH2:31][CH2:30][Si@H:29]([CH2:32][CH2:33][CH3:34])[CH2:28][CH2:27]1>[Cu]I.P(OCC)(OCC)(OCC)=O.C1COCC1>[CH2:32]([Si@H:29]1[CH2:30][CH2:31][C@H:26]([CH2:25][CH2:2][C@H:3]2[CH2:8][CH2:7][C@H:6]([C:9]3[CH:14]=[CH:13][C:12]([C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=4)=[C:11]([F:22])[CH:10]=3)[CH2:5][CH2:4]2)[CH2:27][CH2:28]1)[CH2:33][CH3:34]

Participants

7

Reactant 3

HCID 5462224MagnesiumHCID 178460928HCID 178460928, compoundHCID 178505506HCID 178505506, compound

Product 1

HCID 178460937HCID 178460937, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 6535Triethyl PhosphateCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

38.3 g (0.1 mol) of 4-(trans-4-bromomethylcyclohexyl)-2,4'-difluorobiphenyl 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 triethyl phosphate, 0.1 g of copper (I) iodide and 22.1 g (0.1 mol) of trans-1-bromomethyl-4-n-propyl-4-silacyclohexane. After a conventional after treatment, purification was conducted by means of chromatography to obtain 37.6 g (yield 81.3%) of 4-(trans-4-(2-(trans-4-n-propyl-4-silacyclohexyl)ethyl)cyclohexyl)-2,4'-difluorobiphenyl.

Workup

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

Sources & evidence

ORD record
ord-fd75c14b9a1443c9b0d97e56ce3cc05c
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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