Water → 5-Bromo-2,3-dihydro-1-benzofuran

HRID 1978617Notes

Reaction equation

HRID 1978617 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[Br:16]Br.O>CCCCCC>[Br:16][C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10329DihydrobenzofuranHCID 10340Sodium CarbonateHCID 24408Bromine

Product 1

HCID 27761595-Bromo-2,3-dihydro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

To a mixture of 2,3-dihydrobenzofuran (11.06 g) and sodium carbonate (14.8 g) in hexane (100 ml) was added dropwise at 0° C. a solution of bromine (4.8 ml) in hexane (20 ml) for 1.5 hours, and the mixture was stirred at room temperature for 1 hour. To the mixture was added water, and the mixture was extracted with hexane. The organic layer was washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give gray crystals of 5-bromo-2,3-dihydrobenzofuran (17.64 g).

Workup

  1. extractionthe mixture was extracted with hexane
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-434832157c54453c97c4a04e15c35394
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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