Sodium borohydride → (2-Amino-5-chlorophenyl)(2,5-dichlorophenyl)methanol

HRID 747608Notes

Reaction equation

HRID 747608 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[Cl:18])=[O:10].[BH4-].[Na+]>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]([C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[Cl:18])[OH:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 64422569(2-Amino-5-chlorophenyl)(2,5-dichlorophenyl)methanone

Product 1

HCID 68567338(2-Amino-5-chlorophenyl)(2,5-dichlorophenyl)methanolYield 31.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 6.38 g of (2-amino-5-chlorophenyl)(2,5-dichlorophenyl)methanone dissolved in 50 ml of ethanol are added 2.4 g of sodium borohydride, and the mixture is left for 18 hours at room temperature. The resulting mixture is concentrated and the residue is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated to give 2.016 g of the expected product.

Workup

  1. concentrationThe resulting mixture is concentrated
  2. washwashed with water
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d79a53f8faef4b29b48ac87440ffcc58
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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