Benzyl Bromide → 1610538-08-3

HRID 1486761Notes

Reaction equation

HRID 1486761 reaction equation
[F:1][CH2:2][CH:3]([OH:7])[C:4]([O-:6])=[O:5].[C:8]1([CH:14]([NH3+])C)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(Br)C1C=CC=CC=1>CN(C=O)C.CCOC(C)=O>[F:1][CH2:2][CH:3]([OH:7])[C:4]([O:6][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 90156701HCID 90156701, compound

Product 1

HCID 901571901610538-08-3

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-phenylethanaminium 3-fluoro-2-hydroxypropanoate (11-1) (0.14 g, 0.61 mmol) in DMF (1 mL) was added benzyl bromide (0.087 mL, 0.73 mmol). The mixture was stirred at room temperature overnight, diluted with EtOAc, washed with water and brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (0-50% EtOAc/hexanes) to provide 11-2. HRMS: 198.0688 found, 198.0692 required (M+).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0-50% EtOAc/hexanes)
  6. customto provide 11-2

Sources & evidence

ORD record
ord-111343a2aa644b6eb58e1b5cbd9e7087
Source dataset
uspto-grants-2016_08
Patent number
US09428492B2

Reaction notes

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