Boron tribromide → HCID 14986432, compound

HRID 1613083Notes

Reaction equation

HRID 1613083 reaction equation
C[O:2][C:3]1[C:4]([CH3:34])=[C:5]([C:13](=[O:33])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[C:22]([OH:29])[C:21]=2[CH2:30][CH2:31][CH3:32])[C:6]([CH3:12])=[C:7]([CH3:11])[C:8]=1[O:9]C.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:4]([CH3:34])=[C:5]([C:13](=[O:33])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[C:22]([OH:29])[C:21]=2[CH2:30][CH2:31][CH3:32])[C:6]([CH3:12])=[C:7]([CH3:11])[C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14986431HCID 14986431, compound

Product 1

HCID 14986432HCID 14986432, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 0.98 g (2.07 mmol) of 4-[[6-(3,4-dimethoxy-2,5,6-trimethylphenyl)-6-oxohexyl]oxy]-2-hydroxy-3-propylbenzoic acid in 100 mL of methylene chloride cooled at -75° was added 7 mL (7 mmol) of 1M boron tribromide in methylene chloride. The reaction mixture was stirred at -75° for 30 minutes and then was kept at -20° for 18 hours. Workup as in Example 32 and recrystallization of the crude product from ether-hexane gave 0.51 g, mp 169°-170° of 4-[[6-(3,4-dihydroxy-2,5,6-trimethylphenyl)-6-oxohexyl]oxy]-2-hydroxy-3-propylbenzoic acid.

Workup

  1. waitwas kept at -20° for 18 hours
  2. customWorkup as in Example 32 and recrystallization of the crude product from ether-hexane

Sources & evidence

ORD record
ord-04537f216dbc445d972798368700966d
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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