Bromine → Methyl 2-bromo-5-hydroxy-4-methylbenzoate

HRID 615499Notes

Reaction equation

HRID 615499 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[Br:13]Br>C(Cl)Cl>[Br:13][C:9]1[CH:10]=[C:11]([CH3:12])[C:2]([OH:1])=[CH:3][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 24408BromineHCID 354091Methyl 3-hydroxy-4-methylbenzoate

Product 1

HCID 20428674Methyl 2-bromo-5-hydroxy-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1 g (6 mmoles) of the ester from step a. dissolved in 10 ml of dry CH2Cl2 and cooled in an ice bath was treated dropwise with 0.96 g (6 mmoles) of Br2 in 2 ml CH2Cl2. The reaction flask was sealed and stored at -15° overnight. Gentle swirling of the reaction solution induced crystallization of fine white needles that were collected by filtration and washed with cold CH2Cl2 /hexanes.

Workup

  1. temperaturecooled in an ice bath
  2. customThe reaction flask was sealed
  3. customcrystallization of fine white needles that
  4. filtrationwere collected by filtration
  5. washwashed with cold CH2Cl2 /hexanes

Sources & evidence

ORD record
ord-927cd99e7e33408fa0b3081985cc9c13
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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