Benzoyl Peroxide → Benzoic acid, 4-bromo-3-(bromomethyl)-, ethyl ester

HRID 2197365Notes

Reaction equation

HRID 2197365 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH3:12])[CH:6]=1)[CH3:2].[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH2:12][Br:14])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21729626Ethyl 4-bromo-3-methylbenzoate

Product 1

HCID 22574851Benzoic acid, 4-bromo-3-(bromomethyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromo-3-methyl-benzoic acid ethyl ester (18.24 g, 75.4 mmol), N-bromosuccinimide (14.1 g, 79.2 mmol), and benzoyl peroxide (0.9 g, 3.77 mmol) were combined in CCl4, and the reaction was heated to 80° C. and stirred with a halogen desk lamp shining on it for 6 hours. The mixture was concentrated and partitioned between CH2Cl2 and H2O. The organic layer was separated and washed with H2O and brine, and then dried and concentrated. The residue was triturated with hexane (3×50 mL) and dried to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between CH2Cl2 and H2O
  3. customThe organic layer was separated
  4. washwashed with H2O and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was triturated with hexane (3×50 mL)
  8. customdried

Sources & evidence

ORD record
ord-716171413c9e43b4a67ceb234f7b27f7
Source dataset
uspto-grants-2012_12
Patent number
US08338484B2

Reaction notes

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