Water → 6-(Bromoacetyl)-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17440Notes

Reaction equation

HRID 17440 reaction equation
C([O:3][C:4]([C:6]1[C:7]([F:21])=[C:8]2[O:12][C:11]([N:13]([CH3:15])[CH3:14])=[N:10][C:9]2=[C:16]([C:19]#[N:20])[C:17]=1[CH3:18])=[CH2:5])C.O.[Br:23]N1C(=O)CCC1=O>O1CCCC1>[Br:23][CH2:3][C:4]([C:6]1[C:7]([F:21])=[C:8]2[O:12][C:11]([N:13]([CH3:15])[CH3:14])=[N:10][C:9]2=[C:16]([C:19]#[N:20])[C:17]=1[CH3:18])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 685855916-(1-Ethoxyvinyl)-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 866308506-(Bromoacetyl)-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(1-Ethoxyvinyl)-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-169) (0.51 g, 1.76 mmol) was dissolved in tetrahydrofuran (10 ml), then water (1.0 ml), N-bromosuccinimide (0.30 g, 1.69 g) were added. After stirring at room temperature for 30 minutes, the solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=100:1) to obtain a pale brown solid (0.60 g, 100%).

Workup

  1. customthe solvent was evaporated away under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=100:1)

Sources & evidence

ORD record
ord-bc3a7175d8ca446cac82baa782199c4f
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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