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

HRID 54795
Notes
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Reaction equation

HRID 54795 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 887
Methanol
Solvent
HCID 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-346c59c7b65f4ddba6f8c0daab77efe2
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05623081

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes