2-Bromo-1-(4-fluorophenyl)ethan-1-one → HCID 86621526, compound

HRID 1896703Notes

Reaction equation

HRID 1896703 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:26])[NH:22][CH2:23][CH2:24][NH2:25])([CH3:19])([CH3:18])[CH3:17]>C(O)C>[C:16]([O:20][C:21](=[O:26])[NH:22][CH2:23][CH2:24][NH:25][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])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 187201N-BOC-ethylenediamineHCID 516871Sodium thiocyanate

Product 1

HCID 86621526HCID 86621526, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

2.5 g (11.52 mmol) of 2-bromo-1-(4-fluorophenyl)ethanone and 0.93 g (11.52 mmol) of sodium thiocyanate were stirred in ethanol at 50° C. for 2 h. 1.845 g (11.52 mmol) of (2-aminoethyl)carbamic acid tert-butyl ester were added, and the reaction mixture was stirred at 50° C. for 2 h. After concentrating, water was added, and the mixture was extracted with ethyl acetate. The organic phase was separated and concentrated. Yield: 3.04 g (78%).

Workup

  1. concentrationAfter concentrating
  2. additionwater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic phase was separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-76f6c654e45b47049b0d2dc025e357ed
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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