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

HRID 1600126Notes

Reaction equation

HRID 1600126 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 invacuo. 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 invacuo
  8. customThe residue is purified by chromatography (silica gel: 3-5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-22e93842f52f4b01afc9871fccbbda43
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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