p-Bromobenzenesulfonyl chloride → 4-[(4-Bromobenzene)sulfonyl]morpholine

HRID 1866459Notes

Reaction equation

HRID 1866459 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8083MorpholineHCID 8471Triethylamine

Product 1

HCID 2531284-[(4-Bromobenzene)sulfonyl]morpholineYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromobenzenesulfonylchloride (2.555 g, 10 mmol) in CH2Cl2 (40 mL) was added a solution of triethylamine (1.53 mL, 11 mmol) and morpholine (0.96 mL, 11 mmol) at room temperature under argon atmosphere. The solution was stirred for 2 h and the mixture was purified by flash chromatography eluted with mixed solvent of EtOAc: hexanes (1:2, v/v) to provide 3.028 g (9.89 mmol, yield 98.9%) of N-(4-bromobenzenesulfonyl)morpholine as a white solid.

Workup

  1. customthe mixture was purified by flash chromatography
  2. washeluted with mixed solvent of EtOAc: hexanes (1:2

Sources & evidence

ORD record
ord-cf0201b1ee3448718dd6dfd8bd4e2026
Source dataset
uspto-grants-2009_12
Patent number
US07629375B2

Reaction notes

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