Triethyl Phosphate → HCID 178455407, compound

HRID 1080587Notes

Reaction equation

HRID 1080587 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=3)=[C:10]([F:22])[CH:9]=2)[CH2:4][CH2:3]1.[Mg].P(OCC)(OCC)(OCC)=O.Br[CH2:36][CH2:37][C@H:38]1[CH2:43][CH2:42][Si@H:41]([CH2:44][CH2:45][CH2:46][CH3:47])[CH2:40][CH2:39]1>[Cu]I.C1COCC1>[CH2:44]([Si@H:41]1[CH2:42][CH2:43][C@H:38]([CH2:37][CH2:36][C@H:2]2[CH2:7][CH2:6][C@H:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]4[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=4)=[C:10]([F:22])[CH:9]=3)[CH2:4][CH2:3]2)[CH2:39][CH2:40]1)[CH2:45][CH2:46][CH3:47]

Participants

7

Reactant 4

HCID 6535Triethyl PhosphateHCID 5462224MagnesiumHCID 23364723HCID 23364723, compoundHCID 178455404HCID 178455404, compound

Product 1

HCID 178455407HCID 178455407, compoundYield 72.6%

Reagents, catalysts & solvents 2

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

Procedure

36.9 g (0.1 mol) of 4-(4-bromocyclohexyl)-2,3',4'-trifluorobiphenyl 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 26.3 g (0.1 mol) of trans-1-(2-bromoethyl)-4-n-butyl-4-silacyclohexane. After a conventional after treatment, 4-(trans-4-(2-(trans-4-n-butyl-4-silacyclohexyl)ethyl)cyclohexyl)-2,3',4'-trifluorobiphenyl was obtained. The silacyclohexane rings of the product were a mixture of trans isomers and cis isomers. They were separated by means of chromatography to obtain 34.3 g (yield 72.6%) of the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-99ab53a6d73640a9b8d719c06ec392b4
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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