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

HRID 862950Notes

Reaction equation

HRID 862950 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 el. 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-5dd738dfe960426bb2f82941ace02a2b
Source dataset
uspto-grants-1998_02
Patent number
US05719182

Reaction notes

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