Water → 3-Benzoyloxy-4-chlorobenzyl bromide

HRID 19923

Reaction equation

HRID 19923 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl.C(OCC)C>[Br:18][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:9][C:10](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 167492223-Benzoyloxy-4-chlorotoluene

Product 1

HCID 167478403-Benzoyloxy-4-chlorobenzyl bromide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of benzoic acid 2-chloro-5-methyl-phenyl ester (CAB02124, 2.47 g, 10.0 mmol), N-bromo-succinimide (1.96 g, 11.0 mmol) and dibenzoyl peroxide (10 mg) in carbon tetrachloride (25 mL) was heated to reflux for 1 hour (TLC-control). After cooling to room temperature water (50 mL) and diethyl ether (100 mL) were added. The organic layer was separated, washed with brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc:hexane, 1:40, Rf: 0.21). Yield: 2.012 g (62%) colourless oil, which solidified after a few hours (contains ca. 10% benzoic acid 5-dibromomethyl-2-chloro-phenyl ester).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour (TLC-control)
  3. additionwere added
  4. customThe organic layer was separated
  5. washwashed with brine (20 mL)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography (EtOAc:hexane, 1:40, Rf: 0.21)
  9. waitYield: 2.012 g (62%) colourless oil, which solidified after a few hours

Sources & evidence

ORD record
ord-cf649b7a6cbf4902bba31782f4cdf429
Source dataset
uspto-grants-2010_06
Patent number
US07745472B2

Linked notes

Loading…