Stannous chloride dihydrate → [4-Bromo-2-(trifluoromethyl)phenyl]hydrazine

HRID 1517650Notes

Reaction equation

HRID 1517650 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[N:13]([O-])=O.[Na+].O.O.[Sn](Cl)Cl>Cl.O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][NH2:13])=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:3]=1

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 679604-Bromo-2-(trifluoromethyl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 50988740[4-Bromo-2-(trifluoromethyl)phenyl]hydrazine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

A suspension of 25.6 g (0.11 mol) 4-bromo-2-(trifluoromethyl)-aniline in 125 ml of conc. hydrochloric acid is cooled to −10° C. and a solution of 7.7 g (0.11 mol) sodium nitrite in 125 ml of water is added. The reaction mixture is stirred for 3 hours at −10 to −5° C., then a solution of 103 g (0.46 mol) tin-(II)-chloride-dihydrate in 125 ml of conc. hydrochloric acid is added dropwise. The mixture is stirred for 1 hour at −5° C. The precipitate formed is suction filtered and washed with water. The aqueous mother liquor is extracted with petroleum ether, then made basic with sodium hydroxide. The precipitate formed is extracted with diethyl ether. The organic phase is dried and evaporated to dryness. Yield: 12.9 g

Workup

  1. stirringThe mixture is stirred for 1 hour at −5° C
  2. customThe precipitate formed
  3. filtrationfiltered
  4. washwashed with water
  5. extractionThe aqueous mother liquor is extracted with petroleum ether
  6. customThe precipitate formed
  7. extractionis extracted with diethyl ether
  8. customThe organic phase is dried
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-6cb5c9ac88884b5c9afe285ea6e7a9b6
Source dataset
uspto-grants-2012_07
Patent number
US08232286B2

Reaction notes

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