Benzoyl Peroxide → Methyl 4-(bromomethyl)benzoate

HRID 415172

Reaction equation

HRID 415172 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 7455Methyl 4-methylbenzoateHCID 67184N-bromobutanimide

Product 1

HCID 256687Methyl 4-(bromomethyl)benzoateYield 98.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 4-methylbenzoate 3 (2.9 g, 19.3 mmol) was dissolved in tetrachloromethane (CCl4, 20 mL) at room temperature. N-bromosuccinimide (NBS, 3.5 g, 19.0 mmol) and benzoyl peroxide (BPO, 0.26 g, 1.9 mmol) was added. The resulting mixture was stirred at reflux for 5 hr, then cooled to room temperature, washed with saturated sodium bicarbonate solution and brine, dried with anhydrous sodium sulfate and condensed under vacuum. The residue was purified by silica gel chromatography (petrol ether:ethyl acetate=50:1 to 10:1) to get a white solid of methyl 4-(bromomethyl)benzoate (4.3 g, 97%), LC-MS (ESI) m/z 230 [M+1]+.

Workup

  1. temperatureat reflux for 5 hr
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried with anhydrous sodium sulfate and condensed under vacuum
  4. customThe residue was purified by silica gel chromatography (petrol ether:ethyl acetate=50:1 to 10:1)

Sources & evidence

ORD record
ord-9a473a965e5e4d0b97aca180d7b8ba63
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Linked notes

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