Benzyl Bromide → HCID 86729607, compound

HRID 574235Notes

Reaction equation

HRID 574235 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([OH:15])([CH3:14])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH2:20]([O:15][C:3]([CH3:14])([C:2]([F:16])([F:17])[F:1])[C:4]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:5])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10977790HCID 10977790, compound

Product 1

HCID 86729607HCID 86729607, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) solution of benzyl 3,3,3-trifluoro-2-hydroxy-2-methylpropanoate (Int. D1) (100 mg, 0.403 mmol) in DMF (4 ml) was treated with sodium hydride (16.11 mg, 0.403 mmol) followed by benzyl bromide (0.048 ml, 0.403 mmol) and stirred at 0° C. for 2 h. The reaction mixture was allowed to warm to room temperature and stirring continued for a further 3 hrs. The reaction mixture was partitioned between EtOAc and 0.1M HCl solution. The organic phase was washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as an oil.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirring
  3. waitcontinued for a further 3 hrs
  4. customThe reaction mixture was partitioned between EtOAc and 0.1M HCl solution
  5. washThe organic phase was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc98e88aa8084d7caad1b7f51fc37ec3
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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