Dimethylformamide → 5-Methoxy-2-bromophenylacetyl chloride

HRID 1270786Notes

Reaction equation

HRID 1270786 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([Br:13])=[C:7]([CH2:9][C:10](O)=[O:11])[CH:8]=1.CN(C=O)C.S(Cl)([Cl:21])=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([Br:13])=[C:7]([CH2:9][C:10]([Cl:21])=[O:11])[CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 106340802-(2-Bromo-5-methoxyphenyl)acetic acid

Product 1

HCID 184515295-Methoxy-2-bromophenylacetyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-Methoxy-2-bromophenylacetic acid (56 g, 0.23 mol) is dissolved in CH2Cl2 (350 mL) and a catalytic amount of DMF is added and the solution stirred and cooled to 0° C. Thionyl chloride (41 mL, 0.34 mol) is added dropwise. The reaction mixture is heated at reflux temperature overnight and then cooled to room temperature. Solvents are removed by rotary evaporator. Twice benzene (500 mL) is added to the residual oil and the benzene solution is evaporated by rotary evaporator to remove any additional volatile components. The residual oil is crystallized from hexanes to give 5-methoxy-2-bromophenylacetyl chloride.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux temperature overnight
  3. temperaturecooled to room temperature
  4. customSolvents are removed by rotary evaporator
  5. additionTwice benzene (500 mL) is added to the residual oil
  6. customthe benzene solution is evaporated by rotary evaporator
  7. customto remove any additional volatile components
  8. customThe residual oil is crystallized from hexanes

Sources & evidence

ORD record
ord-c9305daa789e45dc8d26bf2e1c8eed68
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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