Methanol → HCID 66961660, compound

HRID 1362709Notes

Reaction equation

HRID 1362709 reaction equation
[BH4-].[Na+].[Br:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:13])[CH:10]=2)[C:5]1=[O:14].CO.O>O1CCCC1.C(OCC)(=O)C>[Br:3][C@H:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:13])[CH:10]=2)[C@H:5]1[OH:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 110316412-Bromo-5-fluoro-1-indanone

Product 1

HCID 66961660HCID 66961660, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (2.09 g) was added to a solution of 2-bromo-5-fluoroindan-1-one (8.43 g) in a mixture of tetrahydrofuran (120 mL) with methanol (30 mL) while cooling with ice, and the reaction solution was stirred for 20 minutes. Water and ethyl acetate were added to the reaction solution while cooling with ice and the organic layer was partitioned. The resulting organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting solid was washed with heptane to obtain 7.54 g of the title compound. The physical properties of the compound are as follows.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice
  3. customthe organic layer was partitioned
  4. dry with materialThe resulting organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washThe resulting solid was washed with heptane

Sources & evidence

ORD record
ord-91398fc059dc4c7ba3aee665f66bb9cb
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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