3-Bromo-2-hydroxy-6-methoxybenzoic acid → 2-Bromo-5-methoxyphenol

HRID 399236Notes

Reaction equation

HRID 399236 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)C(O)=O>N1C2C(=CC=CC=2)C=CC=1>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:4][C:3]=1[OH:13]

Participants

3

Reactant 1

HCID 134938383-Bromo-2-hydroxy-6-methoxybenzoic acid

Product 1

HCID 134938392-Bromo-5-methoxyphenol

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Procedure

3-Bromo-2-hydroxy-6-methoxybenzoic acid [T. de Paulis et. al., J. Med. Chem., (1985), 28, 1263-1269] (5 g, 0.02 mol) was heated in quinoline (200 mL) at 160° C. for 1 h. On cooling, the product was partitioned between Et2O and 3M HCl. The organic extract was washed with water and brine then dried (MgSO4), filtered and evaporated to give the title compound which was recrystallized from 5% ethyl acetate/hexane (4 g, 97%); m.p. 40°-42° C. Anal. Calc. for C7H7 BrO2 : C, 41.41; H, 3.48. Found C, 41.39; H, 3.37.

Workup

  1. temperatureOn cooling
  2. customthe product was partitioned between Et2O and 3M HCl
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialthen dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-53bfd2b8127647178abb10b7c1bcea7e
Source dataset
uspto-grants-1998_10
Patent number
US05817693

Reaction notes

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