Thionyl Chloride → 2-(Butyloxy)-4-(chloromethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl

HRID 1662321Notes

Reaction equation

HRID 1662321 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([CH2:12]O)[CH:9]=[CH:8][C:7]=1[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[F:22])[CH2:2][CH2:3][CH3:4].S(Cl)([Cl:25])=O>C(Cl)Cl>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([CH2:12][Cl:25])[CH:9]=[CH:8][C:7]=1[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[F:22])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57707020(2-(Butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanol

Product 1

HCID 577055582-(Butyloxy)-4-(chloromethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenylYield 85.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5.3 (0.8800 g, 2.891 mmol) in DCM (15 mL) at 23° C. was added thionyl chloride (0.4218 mL, 5.783 mmol). The reaction mixture was then stirred overnight. The reaction was concentrated and then purified by combiflash (0 to 10% EtOAc/Hexanes) to provide 5.4 (0.7980 g, 85.50% yield).

Workup

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

Sources & evidence

ORD record
ord-5259d1f5ede748d69a9daf1672d55fb3
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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