Thionyl Chloride → Methyl 2-bromo-4-chloro4-oxobutanoate

HRID 1173542Notes

Reaction equation

HRID 1173542 reaction equation
S(Cl)([Cl:3])=O.[Br:5][CH:6]([CH2:11][C:12]([OH:14])=O)[C:7]([O:9][CH3:10])=[O:8]>ClCCl.CN(C)C=O>[Br:5][CH:6]([CH2:11][C:12]([Cl:3])=[O:14])[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 117890713-Bromo-4-methoxy-4-oxobutanoic acid2×

Product 1

HCID 11390578Methyl 2-bromo-4-chloro4-oxobutanoateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (6.54 g, 54.9 mmol) in dichloromethane (7 mL) was added dropwise over 30 minutes to a mixture of 1-methyl hydrogen bromobutanedioate (i.e. the product of Step A) (10 g, 47.4 mmol) and N,N-dimethylformamide (5 drops) in dichloromethane (20 mL) heated at reflux. The mixture was heated at reflux for an additional 60 minutes and then allowed to cool to room temperature. The solvent was removed under reduced pressure to leave the title product as an oil (11 g, about 100% yield).

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureThe mixture was heated
  4. temperatureat reflux for an additional 60 minutes
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-34087a3c05b948d4953d1e21ca11448a
Source dataset
uspto-grants-2010_11
Patent number
US07834186B2

Reaction notes

Loading…