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

HRID 1279316Notes

Reaction equation

HRID 1279316 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 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 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 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-eff33cfb08854c9ba7106afbd73ad9fc
Source dataset
uspto-grants-2002_09
Patent number
US06448260B2

Reaction notes

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