Benzoyl Peroxide → 4-(Bromomethyl)-1-chloro-2-methoxybenzene

HRID 508442Notes

Reaction equation

HRID 508442 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10].[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:9][CH3:10])[CH:4]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 993521-Chloro-2-methoxy-4-methylbenzene

Product 1

HCID 136628594-(Bromomethyl)-1-chloro-2-methoxybenzeneYield 14.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-chloro-3-methoxytoluene (200 mg, 1.28 mmol) in carbon tetrachloride (12 mL) was added N-bromosuccinimide (228 mg, 1.28 mmol) and benzoyl peroxide (31 mg, 0.128 mmol). The mixture was heated at reflux for 2 hours. The reaction mixture was allowed to cool to room temperature and the solvent removed in vacuo. The resulting residue was partitioned between DCM and water. The organic layer was separated, dried over sodium sulphate and evaporated to yield an orange oil. The oil was purified by silica gel chromatography eluting with 30% heptanes in DCM to afford the title compound (45 mg) as a 3.5:1:1 mixture with 4-chloro-3-methoxytoluene and 1-chloro-4-(dibromomethyl)-2-methoxybenzene respectively, which was used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customthe solvent removed in vacuo
  4. customThe resulting residue was partitioned between DCM and water
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customto yield an orange oil
  9. customThe oil was purified by silica gel chromatography
  10. washeluting with 30% heptanes in DCM

Sources & evidence

ORD record
ord-e4b094340ab64f4b8848eb8ab758fba1
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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