Water → 5-Amino-2-(3,3,3-trifluoropropyl)benzofuran

HRID 582619Notes

Reaction equation

HRID 582619 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:8]=2[CH:9]=1.[BH4-].[Na+].O>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].[Pd].ClCCl>[NH2:14][C:11]1[CH:12]=[CH:13][C:7]2[O:6][C:5]([CH2:4][CH2:3][C:2]([F:18])([F:1])[F:17])=[CH:9][C:8]=2[CH:10]=1

Participants

7

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22132946HCID 22132946, compound

Product 1

HCID 221329575-Amino-2-(3,3,3-trifluoropropyl)benzofuran

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.4 g (9.2 mmol) of 2-(3,3,3-trifluoropropyl)-5-nitrobenzofuran, 0.65 g (17 mmol) of sodium borohydride, 45 mg of Adogen 464 and 0.38 g of 10% palladium on carbon containing 50% of water is stirred for 5 hours in 95 ml of dichloromethane and 48 ml of water, then it is filtered on silica and the silica is rinsed with ethanol. The filtrate is then concentrated under reduced pressure and coevaporated with toluene. After chromatography of the residue on a silica column using a 0-30% mixture of ethyl acetate in cyclohexane, 2.0 g of product are obtained.

Workup

  1. filtration48 ml of water, then it is filtered on silica
  2. washthe silica is rinsed with ethanol
  3. concentrationThe filtrate is then concentrated under reduced pressure
  4. customare obtained

Sources & evidence

ORD record
ord-f0da99b1290046519b91d429c421e01a
Source dataset
uspto-grants-1999_07
Patent number
US05925662

Reaction notes

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