Oxalyl chloride → 3-(1-(4-Fluorophenyl)cyclohexyl)propanoyl chloride

HRID 1506381Notes

Reaction equation

HRID 1506381 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][CH2:15][C:16]([OH:18])=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:22])=O>ClCCl.CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][CH2:15][C:16]([Cl:22])=[O:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 666856063-(1-(4-Fluorophenyl)cyclohexyl)propanoic acid

Product 1

HCID 866698893-(1-(4-Fluorophenyl)cyclohexyl)propanoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1-(4-fluorophenyl)cyclohexyl)propanoic acid (Preparation 42A, 209 mg, 0.835 mmol) in dichloromethane (3 mL) at 0° C. was added oxalyl chloride (0.146 mL, 1.670 mmol) followed by a couple of drops of N,N-dimethylformamide, and the mixture was stirred at the same temperature for 20 mins and warmed up to room temperature. The volatiles were evaporated off and the residue was used for next reaction without further purification.

Workup

  1. customThe volatiles were evaporated off
  2. customthe residue was used for next reaction without further purification

Sources & evidence

ORD record
ord-caee0df2a2ac454892698b6e4fb52b60
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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