Sodium borohydride → 5-Amino-2-(3,3,3-trifluoropropyl)benzofuran

HRID 1856816Notes

Reaction equation

HRID 1856816 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+]>[Pd].ClCCl.O>[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

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 22132946HCID 22132946, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 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 (methyl trialkylammonium chloride) and 0.38 g of 5% palladium on carbon containing 50% of water in 95 ml of dichloromethane and 48 ml of water is stirred for 5 hours, 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. By 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. Melting point: 74° C.

Workup

  1. filtrationit 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-1c3910b4c00042bc9275efe2f3d697e3
Source dataset
uspto-grants-2000_11
Patent number
US06143772

Reaction notes

Loading…