N-bromobutanimide → 7-Bromo-4-methoxy-2-(2-methyl-[1,3]-dioxolan-2-yl)benzoxazole

HRID 275804

Reaction equation

HRID 275804 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3([CH3:17])[O:16][CH2:15][CH2:14][O:13]3)[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[Br:18]N1C(=O)CCC1=O>C(#N)C>[Br:18][C:6]1[C:7]2[O:11][C:10]([C:12]3([CH3:17])[O:16][CH2:15][CH2:14][O:13]3)=[N:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 183166394-Methoxy-2-(2-methyl-[1,3]-dioxolan-2-yl)benzoxazole

Product 1

HCID 183166527-Bromo-4-methoxy-2-(2-methyl-[1,3]-dioxolan-2-yl)benzoxazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methoxy-2-(2-methyl-[1,3]-dioxolan-2-yl)benzoxazole (129 m), N-bromosuccinimide (107 mg) and acetonitrile (5 ml) were combined and stirred at room temperature under nitrogen for 4 h. The mixture was partitioned between water (20 ml) and ethyl acetate (20 ml). The aqueous phase was extracted with ethyl acetate (20 ml). The combined organic phases were washed with water (2×50 ml), dried over magnesium sulphate, evaporated in vacuo and purified by flash chromatography eluting with 30% ethyl acetate in hexane to yield the title compound as a white solid (95 mg).

Workup

  1. customThe mixture was partitioned between water (20 ml) and ethyl acetate (20 ml)
  2. extractionThe aqueous phase was extracted with ethyl acetate (20 ml)
  3. washThe combined organic phases were washed with water (2×50 ml)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated in vacuo
  6. custompurified by flash chromatography
  7. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8f21f728eb914cf399d730d3f86ffecc
Source dataset
uspto-grants-2002_03
Patent number
US06353010B1

Linked notes

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