Carbon tetrabromide → 1-(2-Bromoethyl)-2-cyclopropylbenzene

HRID 619804Notes

Reaction equation

HRID 619804 reaction equation
[C:1]1([C:7]2(CO)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P([C:25]2[CH:30]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>C1COCC1.CCOCC>[CH:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=2[CH2:25][CH2:30][Br:32])[CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5205361-Phenylcyclopropanemethanol

Product 1

HCID 218459631-(2-Bromoethyl)-2-cyclopropylbenzeneYield 64.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-phenyl-1-cyclopropane methanol (1 g, 6.8 mmol) in 35 mL of THF is added triphenylphosphine (1.7 g, 7.1 mmol) and carbon tetrabromide (2.34 g, 7.1 mmol). The solution is stirred at ambient temperatures for 5 hours. After this time, the solution is diluted with 100 mL of Et2O. The reaction mixture is filtered and the collected solution is concentrated. The crude product is purified by column chromatography eluting with hexane to afford the title compound (1 g, 4.4 mmol) as an oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe collected solution is concentrated
  3. customThe crude product is purified by column chromatography
  4. washeluting with hexane

Sources & evidence

ORD record
ord-8df947c8f5aa4a79a1c8da12622388e1
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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