Water → 5-((S)-1-azidoethyl)-1,2,3-trifluorobenzene

HRID 1436118Notes

Reaction equation

HRID 1436118 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:10](O)[CH3:11])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].C1C=CC(OP(OC2C=CC=CC=2)([N:22]=[N+:23]=[N-:24])=O)=CC=1.O>C1(C)C=CC=CC=1.N12CCCN=C1CCCCC2>[N:22]([C@H:10]([C:4]1[CH:5]=[C:6]([F:9])[C:7]([F:8])=[C:2]([F:1])[CH:3]=1)[CH3:11])=[N+:23]=[N-:24]

Participants

6

Reactant 3

HCID 962WaterHCID 123414Diphenylphosphoryl azideHCID 57830662HCID 57830662, compound

Product 1

HCID 866126155-((S)-1-azidoethyl)-1,2,3-trifluorobenzene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneSolvent

Procedure

To a solution of (R)-1-(3,4,5-trifluorophenyl)ethanol (3.6 g) and diphenylphosphoric azide (6.0 ml) in toluene (70 ml), 1,8-diazabicyclo[5,4,0]undec-7-ene (4.1 ml) was added dropwise under ice-cooling. The reaction solution was stirred at the same temperature for one hour and at room temperature overnight. Water was added to the reaction solution, and the organic layer was separated. Then, the aqueous layer was subjected to extraction with toluene again. The organic layers were combined and sequentially washed with 1 N hydrochloric acid, water, a saturated sodium bicarbonate solution, and brine. The organic layers were dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (heptane:ethyl acetate=49:1) to obtain 858 mg of the title compound.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. extractionThen, the aqueous layer was subjected to extraction with toluene again
  4. washsequentially washed with 1 N hydrochloric acid, water
  5. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (heptane:ethyl acetate=49:1)

Sources & evidence

ORD record
ord-eccb44a1304b4afc9f1cbea109161a18
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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