Methane → Benzeneacetyl chloride, 4-bromo-

HRID 1739353Notes

Reaction equation

HRID 1739353 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:14])=O.C>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([Cl:14])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 24386Thionyl ChlorideHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 181552Benzeneacetyl chloride, 4-bromo-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

4-Bromophenylacetic acid (100 g, 0.465 mol), thionyl chloride (300 mL) and DMF (about 2 mL) are charged to a 1-liter round bottom 3-necked flask equipped with a reflux condenser and a mechanical stirrer. The reaction mixture is heated under nitrogen to 50° C. for 2 hours, using a charcoal scrubber for escaping gases. The thionyl chloride is evaporated and the product, 4-bromophenylacetyl chloride, is put into an addition funnel with benzene (30 mL)

Workup

  1. customequipped with a reflux condenser and a mechanical stirrer
  2. customThe thionyl chloride is evaporated
  3. customthe product, 4-bromophenylacetyl chloride, is put into an addition funnel with benzene (30 mL)

Sources & evidence

ORD record
ord-fd2dd59d08594de4b06f7ec7c8d43994
Source dataset
uspto-grants-1999_10
Patent number
US05965679

Reaction notes

Loading…