Sulfuryl chloride → Methyl 3-(3-bromo-5-chloro-4-hydroxyphenyl)Propionate

HRID 2378528Notes

Reaction equation

HRID 2378528 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].S(Cl)([Cl:18])(=O)=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[C:6]([Cl:18])[C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 22558720Methyl 3-(3-bromo-4-hydroxyphenyl)propanoate

Product 1

HCID 22559046Methyl 3-(3-bromo-5-chloro-4-hydroxyphenyl)Propionate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of Intermediate 5 (516 mg) in chloroform (5 ml) was added with sulfuryl chloride (177 μl), and stirred at room temperature for 21 hours. The reaction mixture was poured into aqueous saturated sodium hydrogencarbonate (20 ml), and extracted with ethyl acetate. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1) to obtain the title compound (Intermediate 6, 290 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography (Quad, hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-2209c6d047cb4f7f95320d1c3a72ad3a
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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