Water → HCID 54267035, compound

HRID 1816691Notes

Reaction equation

HRID 1816691 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[CH:4][CH:3]=1.[CH3:9][C@H:10]1[O:15][C@@H:14]([CH3:16])[CH2:13][NH:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:12]2[CH2:11][C@H:10]([CH3:9])[O:15][C@H:14]([CH3:16])[CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 99931-Bromo-4-fluorobenzeneHCID 11430Potassium CarbonateHCID 6415002,6-Dimethylmorpholine, cis-

Product 1

HCID 54267035HCID 54267035, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-bromo-4-fluorobenzene (10 g), cis-2,6-dimethylmorpholine (7.74 ml) and potassium carbonate (15.8 g) in dimethylsulfoxide (50 ml) was stirred for 25 hours at 150° C. The reaction mixture was cooled and poured into water (500 ml), and stirred for 10 minutes. The reaction mixture was extracted with ethyl acetate (100 ml×2), washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give a crude yellow oil (680 mg). The crude oil was purified by silica gel chromatography (1:0-10:1 hexane-ethyl acetate) to give 4-(4-bromophenyl)-cis-2,6-dimethylmorpholine (360 mg).

Workup

  1. temperatureThe reaction mixture was cooled
  2. stirringstirred for 10 minutes
  3. extractionThe reaction mixture was extracted with ethyl acetate (100 ml×2)
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto give a crude yellow oil (680 mg)
  8. customThe crude oil was purified by silica gel chromatography (1:0-10:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-88535c49122d4dda9e5d8967466da8d8
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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