Dimethyl Sulfoxide → 4-(5-Bromo-2,3-difluorophenyl)morpholine

HRID 40752Notes

Reaction equation

HRID 40752 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](F)[C:5]([F:9])=[C:6]([F:8])[CH:7]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+].CS(C)=O>O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 6114091-Bromo-3,4,5-trifluorobenzene

Product 1

HCID 595882534-(5-Bromo-2,3-difluorophenyl)morpholineYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-1,2,3-trifluorobenzene (2.5 g, 11.8 mmol), morpholine (1.0 mL, 11.8 mmol), K2CO3 (1.6 g, 11.8 mmol) and DMSO (2 mL) in a sealed tube was heated up to 90° C. for 2.5 h. The reaction mixture was cooled to room temperature and diluted with water. The resulting colorless precipitate was filtered, washed with water, and dried in vacuo to afford 4-(5-bromo-2,3-difluorophenyl)morpholine in 76% yield. 1H NMR (CDCl3, 400 MHz) δ 6.91-6.87 (m, 1H), 6.75-6.72 (m, 1H), 3.80-3.78 (m, 4H), 3.04-3.02 (m, 4H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting colorless precipitate was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-50b89bd3495147078f6a4cd843f35adc
Source dataset
uspto-grants-2013_09
Patent number
US08530480B2

Reaction notes

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