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

HRID 216958

Reaction equation

HRID 216958 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.Br[CH2:13][CH2:14][O:15][CH3:16].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]([CH2:13][CH2:14][O:15][CH3:16])[C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 268532-Benzoxazolinone, 5-bromo-HCID 809722-Bromoethyl methyl ether

Product 1

HCID 579996905-Bromo-3-(2-methoxyethyl)benzo[d]oxazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromobenzo[d]oxazol-2(3H)-one (2.06 g), 1-bromo-2-methoxyethane (1.085 mL) and potassium carbonate (3.99 g) in acetonitrile (15 mL) was heated at 60° C. for 16 h. Water was added and the mixture was extracted with ethyl acetate (3 times). The organic layers were dried over magnesium sulfate, evaporated and purified by flash silica chromatography eluting with 5:1 isohexane/acetone to give the subtitled compound (1.359 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3 times)
  2. dry with materialThe organic layers were dried over magnesium sulfate
  3. customevaporated
  4. custompurified by flash silica chromatography
  5. washeluting with 5:1 isohexane/acetone

Sources & evidence

ORD record
ord-3cbfe3c24c8f4346a5aba6ed41fa7788
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Linked notes

Loading…