Thionyl Chloride → 1-Bromo-4-(chloromethyl)-2-methylbenzene

HRID 1662309Notes

Reaction equation

HRID 1662309 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][C:3]=1[CH3:10].S(Cl)([Cl:13])=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Cl:13])=[CH:4][C:3]=1[CH3:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10987288(4-Bromo-3-methylphenyl)methanol

Product 1

HCID 189606101-Bromo-4-(chloromethyl)-2-methylbenzeneYield 91.32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.1 (2.0 g, 9.947 mmol) in DCM (50 mL) at 23° C. was added thionyl chloride (1.451 mL, 19.89 mmol) and allowed to stir overnight. The reaction was concentrated and then purified by combiflash (0 to 10% EtOAc/hexanes) to provide 1.2 (1.9940 g, 91.32% yield).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by combiflash (0 to 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f47f4f7a08054c05abdd60d670efe7bf
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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