Sodium Hydroxide → 3-Bromo-5-(trifluoromethyl)pyridin-2-amine

HRID 1420712Notes

Reaction equation

HRID 1420712 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[Br:12]Br.[OH-].[Na+]>C(O)(=O)C.CCOCC>[NH2:1][C:2]1[C:7]([Br:12])=[CH:6][C:5]([C:8]([F:9])([F:11])[F:10])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Product 1

HCID 130641553-Bromo-5-(trifluoromethyl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-amino-5-trifluoromethylpyridine (9 g) in acetic acid (75 mL) at r.t. was added bromine (5.8 mL) slowly. After 1 h, the acid was neutralized by the careful addition of sodium hydroxide (10 N) at 0° C. The resulting orange precipitate was dissolved in ether and washed successively with saturated potassium carbonate, saturated Na2SO3 and brine, dried and concentrated. The residual solid was stirred vigorously in hexane for 1 h to provide, after filtration, the title compound as a white solid (10.2 g).

Workup

  1. washwashed successively with saturated potassium carbonate, saturated Na2SO3 and brine
  2. customdried
  3. concentrationconcentrated
  4. customto provide
  5. filtrationafter filtration

Sources & evidence

ORD record
ord-b922af5c1d2246b494197eb82e35ee15
Source dataset
uspto-grants-2000_06
Patent number
US06071936

Reaction notes

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