Water → Benzoic acid, 4-(2,2-dibromoethenyl)-, ethyl ester

HRID 1590399Notes

Reaction equation

HRID 1590399 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][CH:6]=1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33](Br)(Br)([Br:35])[Br:34].O>ClCCl>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:33]([Br:35])[Br:34])=[CH:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 80498Ethyl 4-formylbenzoate

Product 1

HCID 11256090Benzoic acid, 4-(2,2-dibromoethenyl)-, ethyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl-4-formylbenzoate (2.46 g) (ex Lancaster) in dichloromethane (30 ml) under nitrogen was treated with triphenylphosphine (15.7 g) and carbon tetrabromide (9.9 g) at 0°. After 1.5 hours at 25°, water was added and the mixture worked up in the normal manner. Purification by chromatography (silica, ether/hexane) gave ethyl-4-(2,2-dibromoethenyl)benzoate (3.32 g). NMR 1H 8.0(2H,d), 7.50(2H,d), 7.45(1H,s), 3.85(3H,s).

Workup

  1. customPurification by chromatography (silica, ether/hexane)

Sources & evidence

ORD record
ord-fd0918ec09ea4fb98bb00e029ee6ca11
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

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