3-Bromo-2-hydroxy-6-methoxybenzoic acid → 1-Bromo-4-methoxy-2-(methoxymethoxy)benzene

HRID 2288160Notes

Reaction equation

HRID 2288160 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].BrC1C(O)=C([C:18]([O:21][CH3:22])=CC=1)C(O)=O>N1C2C(=CC=CC=2)C=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:18][O:21][CH3:22]

Participants

4

Reactant 2

HCID 134938383-Bromo-2-hydroxy-6-methoxybenzoic acidHCID 134938392-Bromo-5-methoxyphenol

Product 1

HCID 148270371-Bromo-4-methoxy-2-(methoxymethoxy)benzene

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Procedure

1-Bromo-2-hydroxy-4-methoxybenzene. 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 3 M 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 C7H7BrO2 : 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 3 M 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-bf384df311084b2fa7a72045dc454052
Source dataset
uspto-grants-2000_07
Patent number
US06087389

Reaction notes

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