Boron tribromide → HCID 14986378, compound

HRID 1613071Notes

Reaction equation

HRID 1613071 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[C:17]=2[O:24]C)[CH:5]=[CH:4][C:3]=1[C:26](=[O:28])[CH3:27].B(Br)(Br)Br>C(Cl)Cl>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:17]=2[OH:24])[CH:5]=[CH:4][C:3]=1[C:26](=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14986374HCID 14986374, compound

Product 1

HCID 14986378HCID 14986378, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 5.02 g of 1-[2-hydroxy-4-[4-(2,3-dimethoxyphenyl)butoxy]-3-propylphenyl]ethanone in 300 mL of methylene chloride stirred and cooled at -70° was added 39 mL of 1M boron tribromide in methylene chloride. The reaction mixture was stirred at -70° for 30 minutes and kept at -20° for 5.5 hours. Workup as in Example 32 and recrystallization from acetone-hexane gave 3.81 g (82% yield), mp 103°-105° of 1-[2-hydroxy-4-[4-(2,3-dihydroxyphenyl)butoxy]-3-propylphenyl]ethanone.

Workup

  1. temperaturecooled at -70°
  2. waitkept at -20° for 5.5 hours
  3. customWorkup as in Example 32 and recrystallization from acetone-hexane

Sources & evidence

ORD record
ord-02574cd4df284904a2d3a23784e7cea7
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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