Carbon tetrabromide → 1-(2-Bromoethyl)-4-chloro-2-nitrobenzene

HRID 1743869Notes

Reaction equation

HRID 1743869 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:34]>C(Cl)Cl>[Br:34][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 144915122-(4-Chloro-2-nitrophenyl)ethanol

Product 1

HCID 222365841-(2-Bromoethyl)-4-chloro-2-nitrobenzeneYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-chloro-2-nitro-phenyl)-ethanol (63.0 g, 0.31 mole) in methylene chloride (1 L) was added triphenylphosphine (81.9 g, 0.31 mole) and the mixture was cooled to 0° C. Carbon tetrabromide (103.6 g, 0.31 mole) in methylene chloride (100 mL) was added dropwise through an addition funnel. The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue purified by flash column chromatography (silica gel, dichloromethane) to provide 78.0 g of the title compound as a light brown oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash column chromatography (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-a5030b5bbd79498c8c33d8fe7c249935
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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