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

HRID 385326Notes

Reaction equation

HRID 385326 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). 1HNMR (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-4beb0ad174d2457184490062355a32c1
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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