Water → (+/-)-4-Bromo-2-(2,4-difluorophenyl)tetrahydrofuran

HRID 1290406Notes

Reaction equation

HRID 1290406 reaction equation
[Br:1][CH:2]([CH2:14]Br)[CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])[OH:5].[OH-].[Ca+2].[OH-].[Br-].[Ca+2].[Br-].O>C(OCC)(=O)C.CO>[Br:1][CH:2]1[CH2:14][O:5][CH:4]([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=2[F:13])[CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 5360316Calcium BromideHCID 6093208Calcium HydroxideHCID 18923963alpha-(2,3-Dibromopropyl)-2,4-difluorobenzenemethanol

Product 1

HCID 85719042(+/-)-4-Bromo-2-(2,4-difluorophenyl)tetrahydrofuranYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4.5 g of product from Example 164, 1.67 g of calcium hydroxide, 7.5 g of calcium bromide, 25 ml of water and 12 ml of methyl alcohol is stirred and heated at 85° C. overnight. The reaction mixture is cooled, diluted with ethyl acetate and filtered through diatomaceous earth. The layers are separated and the organic layer is washed with saturated sodium chloride, dried, filtered and concentrated in vacuo. The residue is purified by chromatography (silica gel: 3-5% ethyl acetate/hexane) to give 1.96 g of the desired product as a mixture of isomers.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered through diatomaceous earth
  3. customThe layers are separated
  4. washthe organic layer is washed with saturated sodium chloride
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by chromatography (silica gel: 3-5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d8e0b14f80004120ae7728c3e2530add
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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