Boron tribromide → HCID 13050868, compound

HRID 1648950Notes

Reaction equation

HRID 1648950 reaction equation
[OH:1][C:2]1[C:23]2[C:22](=[O:24])[C:9]3[O:10][C:11](=[O:21])[C:12]4[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([O:19]C)[C:13]=4[C:8]=3[C:7](=[O:25])[C:6]=2[CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:19][C:14]1[C:13]2[C:8]3[C:7](=[O:25])[C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([OH:1])[C:23]=4[C:22](=[O:24])[C:9]=3[O:10][C:11](=[O:21])[C:12]=2[CH:17]=[C:16]([CH3:18])[CH:15]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 156387WS-5995 A

Product 1

HCID 13050868HCID 13050868, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In methylene chloride was dissolved 8-hydroxy-1-methoxy-3-methyl-7,12-dihydro-5H-benzo[d]naphtho[2,3-b]pyran-5,7,12-trione (2 g), and under ice-cooling, a methylene chloride solution of boron tribromide (2 ml) was added dropwise. The mixture was further stirred at that temperature for 2 hours, at the end of which time it was washed with water and dried over magnesium sulfate. The solvent was then distilled off to give crude crystals. Recrystallization from methanol gave yellow crystals (1.1 g).

Workup

  1. temperatureunder ice-cooling
  2. washwas washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. customto give crude crystals
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-5796a459e1a84626ad54b70a62943d9d
Source dataset
uspto-grants-1983_11
Patent number
US04414226

Reaction notes

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