Water → 2-Bromo-1-benzofuran

HRID 1501076Notes

Reaction equation

HRID 1501076 reaction equation
[Br:1][C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>O1CCCC1.[Cu]I>[Br:1][C:2]1[O:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 99936722-(2,2-Dibromovinyl)phenol

Product 1

HCID 27762642-Bromo-1-benzofuranYield 92%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(2,2-dibromovinyl)phenol (2.8 g, 10 mmol) in tetrahydrofuran (30 mL) was added copper (I) iodide (0.1 g, 0.5 mmol) and potassium phosphate (4.2 g, 20 mmol). The reaction mixture was stirred at 80° C. under nitrogen atmosphere for 12 hours. After the reaction, the mixture was poured into water (200 mL) and the mixture was extracted with ethyl acetate (200 mL). The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20) to give the pure product 2-bromobenzofuran (1.8 g, 92%).

Workup

  1. customAfter the reaction
  2. extractionthe mixture was extracted with ethyl acetate (200 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20)

Sources & evidence

ORD record
ord-8489cbb7f6b945b39df28733c1ae5143
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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