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

HRID 1662471Notes

Reaction equation

HRID 1662471 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][C:15]=1[CH2:24]O>C(Cl)Cl>[Cl:3][CH2:24][C:15]1[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=[CH:19][C:14]=1[C:7]1[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:6]=1[F:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57707070Methyl 2'-fluoro-2-(hydroxymethyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57706039Methyl 2-(chloromethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (available from Aldrich) (4.46 g, 37.5 mmol) was added to a solution or 66.63A in DCM (6 mL). The reaction mixture was stirred at room temperature for 2 hours and then at 50° C. for 3 hours. After removing solvent, the residue was purified by flash chromatography (silica gel, 1:9 EtOAc/hexane) and gave 66.69A (386 mg) as a colorless oil.

Workup

  1. waitat 50° C. for 3 hours
  2. customAfter removing solvent
  3. customthe residue was purified by flash chromatography (silica gel, 1:9 EtOAc/hexane)

Sources & evidence

ORD record
ord-93124a30a963402596f1931386456722
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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