Ethyl bromoacetate → HCID 59132751, compound

HRID 1993057Notes

Reaction equation

HRID 1993057 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.Br[CH2:21][C:22]([O:24]CC)=[O:23].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([CH:17]([C:18]#[N:19])[CH2:21][C:22]([OH:24])=[O:23])=[CH:15][CH:16]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 2774690{4-[(4-Methoxyphenyl)methoxy]phenyl}acetonitrile

Product 1

HCID 59132751HCID 59132751, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred DMF (10 mL) solution of 2-[4-[(4-Methoxyphenyl)methoxy]phenyl]-acetonitrile (500 mg, 1.97 mmol) was added ethyl bromoacetate (330 μL, 2.96 mmol), followed by K2CO3 (820 mg, 5.9 mmol). The reaction mixture was stirred at room temperature for 2 h, poured into ice water (100 mL), filtered, and dried to a white solid. 20 mg of this white solid in 1:1 THF/1N NaOH in MeOH (4 mL) was stirred for 5 h. The reaction mixture was concentrated, diluted with water (10 mL), washed with EtOAc (5 mL×2). The aqueous layer was acidified with 3N HCl to pH ˜2, extracted with EtOAc (10 mL×2), dried over MgSO4, filtered, and concentrated to a white solid. MS ESI (neg.) m/e: 310.0 (M−1).

Workup

  1. filtrationfiltered
  2. customdried to a white solid
  3. stirring20 mg of this white solid in 1:1 THF/1N NaOH in MeOH (4 mL) was stirred for 5 h
  4. concentrationThe reaction mixture was concentrated
  5. additiondiluted with water (10 mL)
  6. washwashed with EtOAc (5 mL×2)
  7. extractionextracted with EtOAc (10 mL×2)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated to a white solid

Sources & evidence

ORD record
ord-8535d4b0d9b74f9fbaed00c476e16a07
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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