2-Bromo-1-(4-fluorophenyl)ethan-1-one → HCID 86638125, compound

HRID 1931421Notes

Reaction equation

HRID 1931421 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[S-:12][C:13]#[N:14].[Na+].[C:16]([O:20][C:21](=[O:24])[CH2:22][NH2:23])([CH3:19])([CH3:18])[CH3:17]>C(O)C>[C:16]([O:20][C:21](=[O:24])[CH2:22][NH:23][C:13]1[S:12][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=2)[N:14]=1)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 151417Glycine tert-butyl esterHCID 516871Sodium thiocyanate

Product 1

HCID 86638125HCID 86638125, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2 g (9.2 mmol) of 2-bromo-1-(4-fluoro-phenyl)-ethanone and 801.7 mg (9.89 mmol) of sodium thiocyanate in 25 ml of ethanol were stirred at 50° C. for 4 h. 1.2 g (9.2 mmol) of aminoacetic acid tert-butyl ester in 2.5 ml of ethanol were added, and the reaction mixture was stirred at room temperature for 2.5 h and allowed to stand overnight. After evaporation, water and ethyl acetate were added, the organic phase was separated, washed with water, dried and evaporated. Yield: 787 mg.

Workup

  1. waitto stand overnight
  2. customAfter evaporation, water and ethyl acetate
  3. additionwere added
  4. customthe organic phase was separated
  5. washwashed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-ef3ebac0b6a7471a8cd8a6f4dcda2e8e
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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