Bromine → HCID 18352049, compound

HRID 430731Notes

Reaction equation

HRID 430731 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]2[O:12][C:11](=[O:13])[CH:10](O)[C:9]=2[CH:15]=1)([CH3:4])([CH3:3])[CH3:2].[Br:20]Br>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]2[O:12][C:11](=[O:13])[CH:10]([Br:20])[C:9]=2[CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 68508215,7-Di-tert-butyl-3-hydroxy-2-benzofuranone

Product 1

HCID 18352049HCID 18352049, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

12.9 g (0.052 mol) of 5,7-di-tert-butyl-3-hydroxybenzofuranone are dissolved in 50 ml of toluene and treated with 2.9 ml (0.052 mol) of bromine at 30° C. The mixture is subsequently stirred at 60° C. for 30 minutes. The solvent is distilled off by means of a rotary evaporator. 1 g of the crude product is purified by flash chromatography over silica gel (Merck Silicagel 60, 70-230 mesh ASTM; mobile phase: 1:1 hexane/dichloromethane) to leave 0.26 g (36% of theory) of 5,7-di-tert-butyl-3-bromobenzofuranone (XLVII).

Workup

  1. distillationThe solvent is distilled off by means of a rotary evaporator
  2. custom1 g of the crude product is purified by flash chromatography over silica gel (Merck Silicagel 60, 70-230 mesh ASTM; mobile phase: 1:1 hexane/dichloromethane)

Sources & evidence

ORD record
ord-413ae0556e414238b44dcdd389441e89
Source dataset
uspto-grants-2001_11
Patent number
US06323267B1

Reaction notes

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