Water → HCID 59367810, compound

HRID 1643474Notes

Reaction equation

HRID 1643474 reaction equation
P(Br)(Br)[Br:2].[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([S:14]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]2[CH2:23][CH2:24][CH2:25]O)(=[O:16])=[O:15])=[C:9]([CH3:27])[CH:8]=1.O>CN(C=O)C>[Br:2][CH2:25][CH2:24][CH2:23][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][N:17]1[S:14]([C:10]1[C:11]([CH3:13])=[CH:12][C:7]([O:6][CH3:5])=[CH:8][C:9]=1[CH3:27])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 59367771HCID 59367771, compound

Product 1

HCID 59367810HCID 59367810, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

PBr3 (2.64 mmol, 1.5 eq) was added to a solution of 3-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)propan-1-ol (1.76 mmol, 1 eq) in DMF (6 ml) at 0° C. and the mixture was stirred for 30 min. Water (20 ml) was subsequently added and the mixture was extracted with ethyl acetate. The organic phase was washed with water and sat. sodium chloride solution, dried (Na2SO4) and concentrated in vacuo. The crude product obtained in this way was purified by column chromatography (silica gel). Yield: 25%

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with water and sat. sodium chloride solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f66ced3755e54e6081aae68a3b5f1167
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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