Phosphorus tribromide → 4,6-Dimethyl-3-bromobenzofuran

HRID 379331Notes

Reaction equation

[CH3:1][C:2]1[C:7]2[C:8](=O)[CH2:9][O:10][C:6]=2[CH:5]=[C:4]([CH3:12])[CH:3]=1.P(Br)(Br)[Br:14]>>[CH3:1][C:2]1[C:7]2[C:8]([Br:14])=[CH:9][O:10][C:6]=2[CH:5]=[C:4]([CH3:12])[CH:3]=1

Participants

Reactant 2

HCID 24614Phosphorus tribromide

HCID 5955994,6-Dimethyl-3(2H)-benzofuranone

Product 1

HCID 109002874,6-Dimethyl-3-bromobenzofuranYield 60%

Conditions

Temperature: 100 °C

Procedure

4,6-dimethyl-3-benzofuranone (0.90 moles) was slowly added in phosphorus tribromide (30 ml), previously heated to 100° C. The mix is cautiously treated with ice, extracted with methylenechloride. The organic phase is made anhydrous (Na2SO4) and freed from the solvent under reduced pressure to produce 4,6-dimethyl-3-bromobenzofuran (60% yield).

Workup

additionThe mix is cautiously treated with ice
extractionextracted with methylenechloride

Sources & evidence

ORD record: ord-32626ad5e31a49bbb5c2965f67b625d5
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06297387B1

Reaction notes

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