Carbon Tetrachloride → Ethyl 3-bromo-6-methoxy-2-methylbenzoate

HRID 1586587Notes

Reaction equation

HRID 1586587 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([O:13][CH3:14])[CH:5]=[CH:4][CH:3]=1.[Br:15]Br.ClC(Cl)(Cl)Cl>O>[Br:15][C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([C:2]=1[CH3:1])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 24408BromineHCID 5910602-Methoxy-6-methyl-benzoic acid ethyl ester

Product 1

HCID 11022052Ethyl 3-bromo-6-methoxy-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 6-methyl-2-methoxybenzoate (8.4 g, 43.2 mmol), bromine (6.9 g, 43.2 mmol) and tetrachloromethane (170 ml) is stirred at room temperature for 60 hours. The reaction mixture is poured into water and extracted with ethyl acetate. The organic phase is separated and concentrated. The crude product is obtained as a yellow oil, 10.3 g (87% y) and is used without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-764df8cc1a0c436faa7522f56ba7521e
Source dataset
uspto-grants-1999_08
Patent number
US05945567

Reaction notes

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