2-Fluoroethyl bromide → HCID 57392798, compound

HRID 1625547Notes

Reaction equation

HRID 1625547 reaction equation
[Cl-].[C:2]1([CH2:8][C@H:9]([NH2+:11][CH2:12][C:13]#[CH:14])[CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:18][CH2:19][F:20]>CN(C=O)C.O>[F:20][CH2:19][CH2:18][N:11]([C@H:9]([CH3:10])[CH2:8][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:12][C:13]#[CH:14]

Participants

6

Reactant 3

HCID 129822-Fluoroethyl bromideHCID 24758Sodium hydrideHCID 86632948HCID 86632948, compound

Product 1

HCID 57392798HCID 57392798, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[(2R)-1-phenylpropan-2-yl]prop-2-yn-1-aminium chloride (Sigma 100 mg, 0.578 mmol) in dry DMF (2 mL) was added sodium hydride (48.0 mg, 2 mmol). The reaction mixture was stirred at room temperature for 30 min, after which 1-bromo-2-fluoro ethane (0.85 mg, 0.603 mmol) was added. The reaction mixture was stirred over night, diluted with water (10 mL) and extracted with CH2Cl2 (3×15 mL). The organic phase was separated and washed with saturated NaHCO3 (15 ml) and brine (15 ml) and dried over MgSO4 and filtered. The solvent was removed under reduced pressure to obtain the crude product as light yellow oil. The crude product was purified by silica-gel column chromatography (hexane/ether 80:20) and analyzed by NMR, HPLC and LC-MS.

Workup

  1. stirringThe reaction mixture was stirred over night
  2. extractionextracted with CH2Cl2 (3×15 mL)
  3. customThe organic phase was separated
  4. washwashed with saturated NaHCO3 (15 ml) and brine (15 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-32acd9584c754cdba8519f2c4e718193
Source dataset
uspto-grants-2014_07
Patent number
US08784775B2

Reaction notes

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