Water → HCID 18333615, compound

HRID 2269218Notes

Reaction equation

HRID 2269218 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[N+:18]([O-])=O.[BH4-].[Na+].O>CO>[F:1][C:2]1[CH:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[NH2:18]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 18333609HCID 18333609, compound

Product 1

HCID 18333615HCID 18333615, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a vigorously stirred ice-cold mixture of 2-fluoro-4-(4′-methoxy-benzylmercapto)nitrobenzene and NiCl2.6H2O (6.08 g, 25.6 mmol) in CH3OH was added NaBH4 (1.93 g, 51.1 mmol) in portions. The reaction mixture was stirred for 1 h at 0° C., then poured into cold water. The whole was extracted with CH2Cl2 (3×100 ml) and the combined organic layers were dried (Na2SO4), filtered, and evaporated to give 2-fluoro-4-(4′-methoxybenzylmercapto)aniline. MS (Cl) m/e 264 (M+H)+.

Workup

  1. extractionThe whole was extracted with CH2Cl2 (3×100 ml)
  2. dry with materialthe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-bb78c2b675194753a2e82479c967a570
Source dataset
uspto-grants-2001_12
Patent number
US06329395B1

Reaction notes

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