4-Bromo-1-chloro-2-(prop-1-en-2-yl)benzene → 5-Bromo-2-chloroisopropylbenzene

HRID 19800Notes

Reaction equation

HRID 19800 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([C:9]([CH3:11])=[CH2:10])[CH:3]=1>C1(C)C=CC=CC=1.O=[Pt]=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH:9]([CH3:11])[CH3:10])[CH:3]=1

Participants

4

Reactant 1

HCID 685627514-Bromo-1-chloro-2-(prop-1-en-2-yl)benzene

Product 1

HCID 509978695-Bromo-2-chloroisopropylbenzeneYield 72.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 4-bromo-1-chloro-2-isopropenylbenzene (357 mg, 1.54 mmol, 1 eq) and PtO2 (35 mg, 0.15 mmol, 0.1 eq) in 4 ml toluene was stirred under an atmosphere of hydrogen at RT overnight. The reaction mixture was then filtered through celite® and the filtrate was evaporated to dryness to give the desired product (260 mg, 72%). 1H NMR (CDCl3, 300 MHz): 7.39 (d, J=2 Hz, 1H), 7.26-7.16 (m, 2H), 3.35 (sept, J=7 Hz, 1H), 1.23 (d, J=7 Hz, 6H).

Workup

  1. filtrationThe reaction mixture was then filtered through celite®
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-2b82e4e0cc0840f5899eba470048ba56
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Reaction notes

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