Benzonitrile, 4-bromo- → HCID 178447747, compound

HRID 1439826Notes

Reaction equation

HRID 1439826 reaction equation
Br[CH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][Si@H:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:6][CH2:5]1.Br[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1COCC1>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([CH2:2][CH2:3][C@H:4]2[CH2:9][CH2:8][Si@H:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:6][CH2:5]2)=[CH:17][CH:18]=1)#[N:21]

Participants

5

Reactant 2

HCID 12162Benzonitrile, 4-bromo-HCID 178447742HCID 178447742, compound

Product 1

HCID 178447747HCID 178447747, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

250 ml of an organozinc compound (1.0M THF solution) prepared from trans-4-(2-bromoethyl)-1-n-pentyl-1-silacyclohexane was dripped into a mixture of 45.5 g (0.25 mmol) of p-bromobenzonitrile, 500 mg of tetrakis (triphenylphosphine) palladium (0) and 500 ml of THF. After a conventional after treatment, they were separated by means of chromatography to obtain 49.4 g of the target product (yield 66%).

Workup

  1. customAfter a conventional after treatment, they were separated by means of chromatography

Sources & evidence

ORD record
ord-a3d0bec0932b4a3cbaeda5c7e023142b
Source dataset
uspto-grants-1996_03
Patent number
US05496501

Reaction notes

Loading…