Phosphorus tribromide → HCID 59367730, compound

HRID 1643478Notes

Reaction equation

HRID 1643478 reaction equation
P(Br)(Br)[Br:2].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=1[S:13]([N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[CH2:22][CH2:23][CH2:24]O)(=[O:15])=[O:14]>CN(C=O)C.O>[Br:2][CH2:24][CH2:23][CH2:22][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][N:16]1[S:13]([C:7]1[C:8]([CH3:12])=[CH:9][CH:10]=[CH:11][C:6]=1[Cl:5])(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 59367770HCID 59367770, compound

Product 1

HCID 59367730HCID 59367730, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

PBr3 (3.8 mmol, 1.5 eq) was added dropwise to a solution of 3-(1-(2-chloro-6-methylphenylsulfonyl)piperidin-2-yl)propan-1-ol (2.53 mmol, 1 eq) in DMF (6 ml) at 0° C. and the mixture was stirred for 30 min. The reaction mixture was diluted with water (20 ml) and extracted with ethyl acetate (2×20 ml). The combined organic phases were washed with water (30 ml) and saturated sodium chloride solution (20 ml), dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (30% ethyl acetate in hexane). Yield: 25%

Workup

  1. extractionextracted with ethyl acetate (2×20 ml)
  2. washThe combined organic phases were washed with water (30 ml) and saturated sodium chloride solution (20 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e4c867e562fd4c35968ee8d0ad71f440
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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