Carbon Tetrachloride → 2-Bromomethyl-3-chloro-benzoic acid methyl ester

HRID 446026Notes

Reaction equation

HRID 446026 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(Cl)(Cl)(Cl)Cl.[Br:18]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:18][CH2:12][C:3]1[C:2]([Cl:1])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

8

Reactant 4

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 5077673Methyl 3-chloro-2-methylbenzoate

Product 1

HCID 110327262-Bromomethyl-3-chloro-benzoic acid methyl esterYield 100.1%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of methyl 3-chloro-2-methylbenzoate obtained in Example 10b (1 g, 5.42 mmol), carbon tetrachloride (13.3 ml), N-bromosuccinimide (1.06 g, 5.96 mmol) and benzoyl peroxide (3.5 mg, 0.0108 mmol) was heated in a 90° C. oil bath under a nitrogen stream. After three hours and 45 minutes, heating was completed, and the mixture was diluted with water, ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic layer was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and concentrated to give the title compound (1.43 g, yield: 100%).

Workup

  1. temperature45 minutes, heating
  2. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fc01742bf11b45418e5e918a67e2dbb6
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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