Hydrogen Bromide → 4-Bromo-2-phenylfuran

HRID 1403469Notes

Reaction equation

HRID 1403469 reaction equation
O[CH2:2][C:3]#[C:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[BrH:13].O>C1(C)C=CC=CC=1>[Br:13][C:3]1[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:6][CH:2]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 122336204-Hydroxy-1-phenylbut-2-yn-1-one

Product 1

HCID 706650244-Bromo-2-phenylfuranYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-hydroxy-1-phenylbut-2-yn-1-one (3.2 g, crude) in toluene (60 mL) was added HBr (40%, 15 mL). The resulting solution was stirred for 40 min at 50° C. and then the reaction mixture was poured into water (300 mL), extracted with Et2O (4×100 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to give a residue, which was purified by silica gel column chromatography (petroleum ether) to afford 4-bromo-2-phenylfuran as a yellow solid (1.3 g, 50%).

Workup

  1. extractionextracted with Et2O (4×100 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a residue, which
  5. customwas purified by silica gel column chromatography (petroleum ether)

Sources & evidence

ORD record
ord-3b876a5ebd294dedb25b0d55e8182d8e
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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