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

HRID 600329

Reaction equation

HRID 600329 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 subtitle 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-f266f099fe2b4d08929103f9150f70a2
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Linked notes

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