Hydrogen Bromide → Methyl alpha-(2-bromomethylphenyl)but-2-enoate

HRID 725769Notes

Reaction equation

HRID 725769 reaction equation
[BrH:1].CC1C=CC=CC=1O[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17](=[CH:22][CH3:23])[C:18]([O:20][CH3:21])=[O:19]>C(Cl)Cl.C1CCCCC1>[Br:1][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17](=[CH:22][CH3:23])[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 2

HCID 260Hydrogen Bromide2×HCID 53881154Methyl alpha-[2-(2-methylphenyloxymethyl)phenyl]but-2-enoate

Product 1

HCID 54488747Methyl alpha-(2-bromomethylphenyl)but-2-enoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

Hydrogen bromide was passed at -5° C. into a solution of 14.8 g of methyl α-[2-(2-methylphenyloxymethyl)phenyl]but-2-enoate in 250 ml of methylene chloride until it was saturated (about 18 g of HBr). After termination of the reaction (about 2 h at 25° C.), the solvent was distilled off under reduced pressure. The residue thus obtained was taken up in 300 ml of cyclohexane. The solution was washed with 5% strength sodium hydroxide solution and then with water. After drying and concentrating the organic phase, 8 g of the title compound were obtained (m.p.: 64°-66° C.).

Workup

  1. customAfter termination of the reaction (about 2 h at 25° C.)
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue thus obtained
  4. washThe solution was washed with 5% strength sodium hydroxide solution
  5. customAfter drying
  6. concentrationconcentrating the organic phase

Sources & evidence

ORD record
ord-caab919efbb3483693046bbba2c37153
Source dataset
uspto-grants-1998_01
Patent number
US05707936

Reaction notes

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