Methanol → HCID 58563097, compound

HRID 1186160Notes

Reaction equation

HRID 1186160 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH2:8][C:9](O)=[O:10])[CH:7]=1.S(Cl)([Cl:15])=O.CN(C)C=O.CO>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH2:8][C:9]([Cl:15])=[O:10])[CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 35846902-(5-Bromo-2-fluorophenyl)acetic acid

Product 1

HCID 58563097HCID 58563097, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of commercially available 5-bromo-2-fluorophenylacetic acid (compound B1A, [CAS No. 883514-21-4], 6.42 g, 26 mmol) in toluene (52 ml) and thionyl chloride (SOCl2) (4.721 ml, 40 mmol) at 23° C. was added a drop of N,N-dimethylformamide (DMF) and the mixture was stirred at 80° C. for 4 hours (reaction checked by HPLC with product+MeOH). All volatiles were removed by rotary evaporation and the residue was dried in high vacuum to give the title compound as a colorless liquid (7.01 g, 105%), which was used without further purification.

Workup

  1. customAll volatiles were removed by rotary evaporation
  2. customthe residue was dried in high vacuum

Sources & evidence

ORD record
ord-1cacbbe8bc0a4e71bb30f0c81ac83ffb
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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