Morpholine → 4-((3-Bromo-4-fluorophenyl)sulfonyl)morpholine

HRID 930916Notes

Reaction equation

HRID 930916 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([S:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 218867333-Bromo-4-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 867210704-((3-Bromo-4-fluorophenyl)sulfonyl)morpholineYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-4-fluorobenzene-1-sulfonyl chloride (0.44 g, 1.609 mmol) in tetrahydrofuran (10 mL) was treated with morpholine (0.294 g, 3.38 mmol). The reaction mixture was stirred for 16 hours at ambient temperature. The solvent was removed, and the residue was loaded onto a silica gel column and eluted with 20% ethyl acetate in hexanes to give the title compound (0.45 g, 1.388 mmol, 86% yield).

Workup

  1. customThe solvent was removed
  2. washeluted with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4ec98ea26d7042daab1e68f869d4ec56
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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