Oxalyl chloride → [R]-(-)-2-(p-fluorophenyl)-3-methylbutyryl chloride

HRID 892808Notes

Reaction equation

HRID 892808 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH:12]([CH3:14])[CH3:13])[C:9](O)=[O:10])=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:18])=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH:12]([CH3:14])[CH3:13])[C:9]([Cl:18])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 10888841(2R)-2-(4-fluorophenyl)-3-methylbutanoic acid

Product 1

HCID 53636491[R]-(-)-2-(p-fluorophenyl)-3-methylbutyryl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 32.3 g (0.165 mol) of [R]-(-)-2-(p-fluorophenyl)-3-methylbutyric acid in 250 ml of abs. methylene chloride was treated with 27.3 ml of oxalyl chloride. After stirring at room temperature for 4 hours and evaporation of the solvent under reduced pressure, [R]-(-)-2-(p-fluorophenyl)-3-methylbutyryl chloride was obtained as an oil, b.p. 100°/65 Pa; [α]D20 =-53.2° (c=1, chloroform).

Workup

  1. customevaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-780617868d24437b89f4ad6206afb1b4
Source dataset
uspto-grants-1992_06
Patent number
US05120759

Reaction notes

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