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

HRID 1828758Notes

Reaction equation

HRID 1828758 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-288c9b8510e042a481f919bf068a28fe
Source dataset
uspto-grants-2006_06
Patent number
US07060715B2

Reaction notes

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