Water → 5-Bromo-3-(3-methoxypropyl)benzo[d]oxazol-2(3H)-one

HRID 216931

Reaction equation

HRID 216931 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.CS(O[CH2:17][CH2:18][CH2:19][O:20][CH3:21])(=O)=O.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 268532-Benzoxazolinone, 5-bromo-HCID 116939633-Methoxypropyl methanesulfonate

Product 1

HCID 595686035-Bromo-3-(3-methoxypropyl)benzo[d]oxazol-2(3H)-oneYield 102%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-bromobenzo[d]oxazol-2(3H)-one (1.1 g), 3-methoxypropyl methanesulfonate (1.297 g) and potassium carbonate (2.131 g) in acetonitrile (25 mL) was heated at 70° C. for 16 h. Water was added and the mixture was extracted with ethyl acetate (3 times). The organic layers were dried (MgSO4), evaporated and purified by flash chromatography (silica, isohexane-acetone (5:1) as eluent) to give the sub-titled compound (1.50 g) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3 times)
  2. dry with materialThe organic layers were dried (MgSO4)
  3. customevaporated
  4. custompurified by flash chromatography (silica, isohexane-acetone (5:1) as eluent)

Sources & evidence

ORD record
ord-fec2372dda034954aea9c090d9c7a41d
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Linked notes

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