Bromine → HCID 19047048, compound

HRID 1780586Notes

Reaction equation

HRID 1780586 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:6]=[CH:5][N:4]=1.C([O-])(=O)C.[Na+].[Br:29]Br>C(O)(=O)C.O>[Br:29][C:13]1[CH:12]=[CH:11][C:10]([NH:15][C:16](=[O:21])[C:17]([CH3:19])([CH3:20])[CH3:18])=[C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([C:2]([F:1])([F:22])[F:23])[N:8]=2)[CH:14]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 19047032HCID 19047032, compound

Product 1

HCID 19047048HCID 19047048, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

3 g N-[2-[2-(trifluoromethyl)4-pyrimidinyl]phenyl]-2,2-dimethylpropanamide was dissolved in 30 mL glacial acetic acid, 5 g anhydrous sodium acetate was added, and a solution of 2.8 g bromine in 5 mL acetic acid was added dropwise with stirring over 1 h. The reaction mixture was stirred at room temperature overnight, after which it was diluted with water. The precipitate was collected by filtration, washed well with water, then with hexane, and was dried in a vacuum oven overnight to yield 3.3 g of the title compound melting at 153°-157° C. 1H NMR (CDCl3): δ 1.28 (s,9H), 7.40-8.4 (6H), 10.6 (s,1H,NH).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. filtrationThe precipitate was collected by filtration
  3. washwashed well with water
  4. dry with materialwith hexane, and was dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-6e2bc3b4a6894d489db4d0d583233b22
Source dataset
uspto-grants-1997_05
Patent number
US05631206

Reaction notes

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