(Diethylamino)sulfur trifluoride → Tert-butyl 3-(3-bromophenyl)-3-fluoropropylcarbamate

HRID 1021151Notes

Reaction equation

HRID 1021151 reaction equation
C(N(S(F)(F)[F:7])CC)C.[Br:10][C:11]1[CH:12]=[C:13]([CH:17](O)[CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:14]=[CH:15][CH:16]=1>>[Br:10][C:11]1[CH:12]=[C:13]([CH:17]([F:7])[CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 57608439Tert-butyl 3-(3-bromophenyl)-3-hydroxypropylcarbamate

Product 1

HCID 66743475Tert-butyl 3-(3-bromophenyl)-3-fluoropropylcarbamate

Conditions

Temperature
-78 °C

Procedure

Diethylaminosulphur trifluoride (DAST) is added under an inert atmosphere to a cold (−78° C.) solution of alcohol 39. The reaction mixture is stirred at −78° C. until no starting material is seen by TLC. The reaction mixture is partitioned between water and EtOAc, and aqueous layer is extracted with EtOAc. The combined organic layers are washed with brine and dried over anhydrous MgSO4. Purification by flash chromatography gives tert-butyl 3(3-bromophenyl)-3-fluoropropylcarbamate.

Workup

  1. customThe reaction mixture is partitioned between water and EtOAc, and aqueous layer
  2. extractionis extracted with EtOAc
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-608686a0bb064464870ac68efd8c5df0
Source dataset
uspto-grants-2014_05
Patent number
US08716529B2

Reaction notes

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