Methanol → methyl 2-bromo-3-chlorobenzoate

HRID 1481361Notes

Reaction equation

HRID 1481361 reaction equation
[Br:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>C(Cl)Cl.CN(C=O)C>[CH3:16][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([Cl:11])[C:2]=1[Br:1]

Participants

6

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 331232-bromo-3-chlorobenzoic acid

Product 1

HCID 53751442methyl 2-bromo-3-chlorobenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-3-chlorobenzoic acid (7.29 mmol) in 20 mL DCM and 1 mL DMF was added 1.06 mL thionyl chloride. After stirring at RT overnight, 5 mL MeOH were added and stirring was continued at RT for 1 h. The reaction mixture was cooled in an ice bath, quenched by adding a sat. aq. NaHCO3 solution and extracted twice with DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as colorless oil.

Workup

  1. stirringstirring
  2. waitwas continued at RT for 1 h
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. customquenched
  5. additionby adding a sat. aq. NaHCO3 solution
  6. extractionextracted twice with DCM
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7abd6da93a9942c59eeb9ef8012602fc
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

Loading…