Water → 5-bromo-2-({[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfanyl)-1,3-oxazole

HRID 1511519Notes

Reaction equation

HRID 1511519 reaction equation
[F:1][CH:2]([F:21])[O:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[CH2:14][S:15][C:16]1[O:17][CH:18]=[CH:19][N:20]=1.[Br:22]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:22][C:18]1[O:17][C:16]([S:15][CH2:14][C:5]2[C:6]([C:10]([F:12])([F:13])[F:11])=[N:7][N:8]([CH3:9])[C:4]=2[O:3][CH:2]([F:1])[F:21])=[N:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 462224072-({[5-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfanyl)-1,3-oxazole

Product 1

HCID 866510125-bromo-2-({[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfanyl)-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-({[5-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfanyl)-1,3-oxazole (1.24 g, 4 mmol) is initially charged in 20 ml of dimethylformamide. N-Bromosuccinimide (0.892 g, 5 mmol) is then added a little at a time with stirring. The mixture is stirred at 40° C. for a further 6 hours. For work-up, the reaction mixture is added to water and extracted twice with dichloromethane, and the extracts are then washed with water and finally with saturated NaCl solution. The combined organic phases are dried over magnesium sulfate, filtered off and concentrated. The crude product is purified chromatographically (heptane:ethyl acetate, gradient 10:0 to 7:3). This gives 0.70 g of product (43.2% of theory).

Workup

  1. stirringThe mixture is stirred at 40° C. for a further 6 hours
  2. extractionextracted twice with dichloromethane
  3. washthe extracts are then washed with water and finally with saturated NaCl solution
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated
  7. customThe crude product is purified chromatographically (heptane:ethyl acetate, gradient 10:0 to 7:3)

Sources & evidence

ORD record
ord-af38bd83ca034bde98811b7ebc62f85c
Source dataset
uspto-grants-2012_07
Patent number
US08216973B2

Reaction notes

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