Ethyl bromoacetate → HCID 117662380, compound

HRID 1428389Notes

Reaction equation

HRID 1428389 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](=[O:11])[NH:8][C:7]=2[CH:12]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CC(C)=O>[O:11]=[C:9]1[N:8]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:7]2[CH:12]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=[CH:5][C:6]=2[O:10]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 268522-Benzoxazolinone, 5-(trifluoromethyl)-

Product 1

HCID 117662380HCID 117662380, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 5-trifluoromethyl-1,3-benzoxazol-2(3H)-one (999 mg) and acetone (25 mL) were added K2CO3 (1.02 g) and ethyl bromoacetate (708 μL) at room temperature, followed by heating to reflux for 4 hours. The reaction mixture was filtered while hot, and washed with acetone. The filtrate and the washed solution were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=100/0-75/25) to obtain ethyl [2-oxo-5-(trifluoromethyl)-1,3-benzoxazol-3(2H)-yl]acetate (1.33 g).

Workup

  1. temperatureby heating
  2. temperatureto reflux for 4 hours
  3. filtrationThe reaction mixture was filtered while hot, and
  4. washwashed with acetone
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: Hex/EtOAc=100/0-75/25)

Sources & evidence

ORD record
ord-0d224dab88bc4eb0a24db75fe33c63e0
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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