N-bromobutanimide → Methyl 2-(3-methoxy-4-nitrophenyl)-5-methyl-1,3-oxazole-4-carboxylate

HRID 43611Notes

Reaction equation

HRID 43611 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[O:13][CH:14]([CH3:21])[CH:15]([C:17]([O:19][CH3:20])=[O:18])[N:16]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].BrN1C(=O)CCC1=O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[O:13][C:14]([CH3:21])=[C:15]([C:17]([O:19][CH3:20])=[O:18])[N:16]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67548884Methyl 2-(3-methoxy-4-nitrophenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate

Product 1

HCID 68405823Methyl 2-(3-methoxy-4-nitrophenyl)-5-methyl-1,3-oxazole-4-carboxylateYield 51.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The same operation as in Example (96a) was performed using methyl 2-(3-methoxy-4-nitrophenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxylate obtained in Example (105b) (3.6 g, 12.2 mmol), α,α-bisisobutyronitrile (99 mg, 0.6 mmol), N-bromosuccinimide (2.40 g, 13.5 mmol) and benzene (50 mL). Purification by silica gel column chromatography (elution solvent: chloroform/methanol=99/1, 98/2, 96/4, 94/6) gave 1.84 g of the title compound as a light yellow solid (51%).

Workup

  1. customPurification
  2. washby silica gel column chromatography (elution solvent: chloroform/methanol=99/1, 98/2, 96/4, 94/6)

Sources & evidence

ORD record
ord-4291d4d99ba6472ca8407c18fb71ae41
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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