Water → (2S)-3-(2-Azidopropyl)-1,2,4,5-tetrafluorobenzene

HRID 920462Notes

Reaction equation

HRID 920462 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([CH2:10][C@H:11](S(C)(=O)=O)[CH3:12])[C:3]=1[F:17].[N-:18]=[N+:19]=[N-:20].[Na+].O>CN(C=O)C>[N:18]([C@@H:11]([CH3:12])[CH2:10][C:4]1[C:5]([F:9])=[C:6]([F:8])[CH:7]=[C:2]([F:1])[C:3]=1[F:17])=[N+:19]=[N-:20]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86663207HCID 86663207, compound

Product 1

HCID 86663208(2S)-3-(2-Azidopropyl)-1,2,4,5-tetrafluorobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2R)-1,2,4,5-tetrafluoro-3-(2-(methylsulfonyl)propyl)benzene (2.3 g, 8.03 mmol) in anhydrous DMF (10 mL) was added sodium azide (1.045 g, 16.07 mmol) and the solution was heated to 80° C. and stirred for 2 h. Then, the temperature was cooled to rt and 20 mL of water was added, extracted with EtOAc/hexane (1/1 v/v), dried over anhydrous MgSO4 and evaporated to give crude oil, which was passed through silica gel pad and evaporated under reduced pressure to give the product. This was used as starting material for next reduction without more purification.

Workup

  1. temperatureThen, the temperature was cooled to rt
  2. extractionextracted with EtOAc/hexane (1/1 v/v)
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated
  5. customto give crude oil, which
  6. customevaporated under reduced pressure
  7. customto give the product
  8. customwithout more purification

Sources & evidence

ORD record
ord-315272e12f6c42f9938aa36b4030cd39
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Reaction notes

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