Thionyl Chloride → 2-Chloro-1-(1-chloro-ethyl)-4-methoxy-benzene

HRID 2386801Notes

Reaction equation

HRID 2386801 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[CH:14](O)[CH3:15]>C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[CH:14]([Cl:3])[CH3:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 217555931-(2-Chloro-4-methoxy-phenyl)-ethanol

Product 1

HCID 610834622-Chloro-1-(1-chloro-ethyl)-4-methoxy-benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.9 ml) was added to a solution of 1-(2-chloro-4-methoxy-phenyl)-ethanol (2 g) in DCM (5 ml) at 0° C. The mixture was allowed to warm to room temperature and then stirred for 1 h. The mixture was concentrated to an oil and filtered over SiO2 (1 g) to give the title compound (2 g) as a light brown oil. 1H NMR (300 MHz, CDCl3) δ 7.5 (1H, d), 6.8-6.9 (2H, m), 5.5 (1H, q), 3.8 (3H, s), 1.8 (3H, d).

Workup

  1. concentrationThe mixture was concentrated to an oil
  2. filtrationfiltered over SiO2 (1 g)

Sources & evidence

ORD record
ord-a7385e4b2460492da49392503f98bbab
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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