Morpholine → 4-(4-Bromo-2-trifluoromethyl-benzenesulfonyl)-morpholine

HRID 1098747Notes

Reaction equation

HRID 1098747 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(N(CC)CC)C.C(OCC)(=O)C>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)(=[O:10])=[O:9])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 27786084-Bromo-2-(trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 473151804-(4-Bromo-2-trifluoromethyl-benzenesulfonyl)-morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-bromo-2-trifluoromethyl-benzenesulfonyl chloride (5.00 g, 15.46 mmol) in THF (5 ml) was added to a solution of morpholine (1.62 ml, 18.55 mmol) and triethylamine (2.15 ml, 15.46 mmol) in tetrahydrofurane. The reaction mixture was stirred for 12 h at RT. Ethyl acetate (80 ml) was added, the organic phase was separated and washed with water (20 ml), hydrochloric acid (1 M, 20 ml) and brine (20 ml) and dried over sodium sulphate. After evaporation the product was obtained (5.708 g, 99%) and used in the next step without further purification.

Workup

  1. customthe organic phase was separated
  2. washwashed with water (20 ml), hydrochloric acid (1 M, 20 ml) and brine (20 ml)
  3. dry with materialdried over sodium sulphate
  4. customAfter evaporation the product
  5. customwas obtained (5.708 g, 99%)
  6. customused in the next step without further purification

Sources & evidence

ORD record
ord-c271db019ed541ca9b07df318b890985
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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