Thionyl Chloride → 2-Bromo-5-(chloromethyl)phenyl butyl ether

HRID 1662337Notes

Reaction equation

HRID 1662337 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH2:13][CH3:14].S(Cl)([Cl:17])=O>C(Cl)Cl>[CH2:11]([O:10][C:3]1[CH:4]=[C:5]([CH2:8][Cl:17])[CH:6]=[CH:7][C:2]=1[Br:1])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57705850(4-Bromo-3-(butyloxy)phenyl)methanol

Product 1

HCID 577063052-Bromo-5-(chloromethyl)phenyl butyl etherYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 20.2 (659.3 mg, 2544 μmol) in DCM (15 mL) at 23° C., was added thionyl chloride (371 μL, 5088 μmol). The resulting mixture was stirred overnight. The reaction was concentrated and then purified by combiflash (0 to 10% EtOAc/Hexanes) to provide 20.3 (650 mg, 92.0% yield).

Workup

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

Sources & evidence

ORD record
ord-196a25fc8e724315a14d556eab312c94
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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