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

HRID 43596Notes

Reaction equation

HRID 43596 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[O:13][CH2:14][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][CH:14]=[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 68406207Methyl 2-(3-methoxy-4-nitrophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate

Product 1

HCID 67549178Methyl 2-(3-methoxy-4-nitrophenyl)-1,3-oxazole-4-carboxylateYield 85.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The same operation as in Example (96a) was performed using methyl 2-(3-methoxy-4-nitrophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate obtained in Example (102b) (1.72 g, 6.14 mmol), α,α-bisisobutyronitrile (50 mg, 0.3 mmol), N-bromosuccinimide (1.20 g, 6.75 mmol) and benzene (30 mL). Purification by silica gel column chromatography (elution solvent: chloroform/methanol=99/1, 98/2, 95/5) gave 1.46 g of the title compound as a light yellow solid (85%).

Workup

  1. customPurification
  2. washby silica gel column chromatography (elution solvent: chloroform/methanol=99/1, 98/2, 95/5)

Sources & evidence

ORD record
ord-08def9d8b4154018b91bc85d64520593
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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