Bromine → HCID 22625618, compound

HRID 277669Notes

Reaction equation

HRID 277669 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]1[N:12]=[C:13]([CH3:19])[N:14]([CH:16]([F:18])[F:17])[CH:15]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:15]1[N:14]([CH:16]([F:17])[F:18])[C:13]([CH3:19])=[N:12][C:11]=1[C:5]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=1[Cl:3]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 516892Sodium BicarbonateHCID 22625606HCID 22625606, compound

Product 1

HCID 22625618HCID 22625618, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

Bromine (0.54 g, 3.1 mmol), in 7 ml of methylene chloride, was added dropwise to a solution of 0.9 g (3.2 mmol) of 4-(2,4-dichlorophenyl)-1-difluoromethyl-2-methylimidazole stirring in 35 ml of methylene chloride. The reaction mixture was stirred at room temperature overnight. Another 0.3 g of bromine, in 5 ml of methylene chloride, were added and the reaction stirred overnight. Methylene chloride (250 ml) and saturated sodium bicarbonate (200 ml) were added and the organic layer separated and washed with saturated sodium bicarbonate and brine followed by drying over magnesium sulfate. Evaporating in vacuo gave a red oil residue. Flash chromatography on silica gel (20:1-10:1-5:1-3:1 hexane/ethyl acetate) afforded 0.7 g of 5-bromo-4-(2,4-dichlorophenyl)-1-difluoromethyl-2-methylimidazole as a white solid (m.p. 81-83° C.). NMR (CDCl3, 200 MHz) δ: 2.65 (s, 3H), 7.20 (t, 1H), 7.27-7.40 (m, 2H), 7.52 (s, 1H).

Workup

  1. stirringthe reaction stirred overnight
  2. customthe organic layer separated
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialby drying over magnesium sulfate
  5. customEvaporating in vacuo
  6. customgave a red oil residue

Sources & evidence

ORD record
ord-692e4209b8fd4bc18412927a99af2ac8
Source dataset
uspto-grants-2002_03
Patent number
US06358885B1

Reaction notes

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