Methanol → Ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)acetate

HRID 1512381Notes

Reaction equation

HRID 1512381 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].CO.S(Cl)([Cl:20])(=O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[C:6]([Cl:20])[C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 24648Sulfuryl chlorideHCID 18620106Ethyl 2-(3-bromo-4-hydroxyphenyl)acetate

Product 1

HCID 57995583Ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)acetateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 2-(3-bromo-4-hydroxyphenyl)acetate (20 g, 0.076 molo) in 200 ml of DCM was added MeOH (3.4 ml, 0.84 mol) and the mixture was refluxed. Sulfuryl chloride (6.8 ml 0.846 mol) was slowly added under over a period of 10 min. The reaction mixture was refluxed for a further 5 h. Upon completion of reaction, the mixture was poured onto crushed ice and extracted with DCM (×2). The combined organic layer were washed with 10% NaHCO3 solution and water, dried over Na2SO4, filtered and evaporated under vacuum to give ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)acetate in 60% yield. (13.6 g). 1H NMR (CDCl3): 7.37 (s,1H); 7.27 (s,1H); 5.68 (bs, 1H); 4.16 (q, 2H); 3.48 (s, 2H); 1.29 (t, 3H).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureThe reaction mixture was refluxed for a further 5 h
  3. customUpon completion of reaction
  4. additionthe mixture was poured
  5. customonto crushed ice
  6. extractionextracted with DCM (×2)
  7. washThe combined organic layer were washed with 10% NaHCO3 solution and water
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated under vacuum

Sources & evidence

ORD record
ord-7e20460adf404ae69cb6744b2e345b65
Source dataset
uspto-grants-2012_07
Patent number
US08217064B2

Reaction notes

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