Boron tribromide → 4-[6-(2,3-Dihydroxyphenyl)hexyloxy]benzoic acid

HRID 1613065Notes

Reaction equation

HRID 1613065 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[C:18]=2[O:25]C)=[CH:6][CH:5]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:25][C:18]1[C:19]([OH:23])=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:27])=[O:2])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 149863444-[6-(2,3-Dimethoxyphenyl)hexyloxy]benzoic acid methyl ester

Product 1

HCID 149863454-[6-(2,3-Dihydroxyphenyl)hexyloxy]benzoic acidYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 0.80 g (2.2 mmol) of 4-[6-(2,3-dimethoxyphenyl)hexyloxy]benzoic acid methyl ester in 25 mL of methylene chloride stirred and cooled at -70° was added 8.0 mL of 1M boron tribromide in methylene chloride. The reaction mixture was stirred at -70° for 30 minutes and at -20° for 7 hours. Workup as in example 32 and recrystallization from ethyl acetate-hexane gave 0.30 g (42% yield), mp 170°-172° of 4-[6-(2,3-dihydroxyphenyl)hexyloxy]benzoic acid.

Workup

  1. temperaturecooled at -70°
  2. customWorkup as in example 32 and recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-334cd04ac9234007b663a989c08731b4
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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