Carbon Tetrachloride → Methyl 4-(bromomethyl)-2-chlorobenzoate

HRID 2355271Notes

Reaction equation

HRID 2355271 reaction equation
C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:19][O:20][C:21](=[O:30])[C:22]1C=[CH:26][C:25]([CH3:28])=[C:24](Cl)[CH:23]=1.[Br:31]N1C(=O)CCC1=O.[C:39]([Cl:43])(Cl)(Cl)Cl>>[CH3:19][O:20][C:21](=[O:30])[C:22]1[CH:23]=[CH:24][C:25]([CH2:28][Br:31])=[CH:26][C:39]=1[Cl:43]

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 2801405Methyl 3-Chloro-4-methylbenzoate

Product 1

HCID 22072833Methyl 4-(bromomethyl)-2-chlorobenzoate

Procedure

Add benzoyl peroxide (308 mg, 1.27 mmol) to a mixture of methyl-3-chloro-4-metylbenzoate (4.7 g, 25.5 mmol) and N-bromosuccinimide (4.98 g, 28.00 mmol) in anhydrous carbon tetrachloride (100 mL). Reflux the reaction mixture for 4 hrs and cool to room temperature. Filter the reaction mixture and concentrate the filtrate to provide the title compound as a crude oil (7.6 g, 28.8 mmol). MS (m/z): 264 (M+1).

Workup

  1. temperatureReflux the reaction mixture for 4 hrs
  2. filtrationFilter the reaction mixture
  3. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-db34ca72447f495d90c64b8d4dd06c95
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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