Water → HCID 59693636, compound

HRID 899095Notes

Reaction equation

HRID 899095 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10].[CH2:13]([N:20]1[CH2:25][CH2:24][O:23][CH:22]([C:26]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:28][O:27]2)[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>O1CCCC1.[Cu](I)I>[CH2:13]([N:20]1[CH2:25][CH2:24][O:23][CH:22]([C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([OH:27])[CH2:28][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:9]([F:12])([F:11])[F:10])[CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 9806Benzene, 1-bromo-2-(trifluoromethyl)-HCID 5462224MagnesiumHCID 596936444-Benzyl-2-(2-phenyloxiran-2-yl)morpholine

Product 1

HCID 59693636HCID 59693636, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a suspension of magnesium turnings in tetrahydrofuran (2 mL) at room temperature under nitrogen atmosphere was added a solution of 1-bromo-2-trifluoromethyl-benzene (7.6 g, 5 equiv., available from Acros) in tetrahydrofuran (32 mL) and the mixture was stirred for an hour. The solution was cooled to −78° C. and copper iodide (646 mg) was added followed by dropwise addition of a solution of 4-Benzyl-2-(2-phenyl-oxiranyl)-morpholine (2 g, 1 equiv.) in tetrahydrofuran (10 mL). The resulting mixture was warmed to room temperature over 2 hours and then treated with water (10 mL). The solution was extracted with diethyl ether, the organic phase dried with MgSO4, and evaporated in vacuo. The crude material was purified using a column chromatography on silica gel eluting with a mixture of ethyl acetate/heptane (10/90) to give 352 mg of the title compound as a colourless oil (12%). LCMS (6 minutes method) [M+H]+=442 @ Rt 3.05 min. major peak.

Workup

  1. temperatureThe resulting mixture was warmed to room temperature over 2 hours
  2. extractionThe solution was extracted with diethyl ether
  3. dry with materialthe organic phase dried with MgSO4
  4. customevaporated in vacuo
  5. customThe crude material was purified
  6. additionwith a mixture of ethyl acetate/heptane (10/90)

Sources & evidence

ORD record
ord-4e3b337e8f8e4a07a8b9e482dff750ae
Source dataset
uspto-grants-2008_04
Patent number
US07354920B2

Reaction notes

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