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

HRID 658891Notes

Reaction equation

HRID 658891 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-c26c77f0e26f40cc8e8b14492671d248
Source dataset
uspto-grants-2011_12
Patent number
US08076516B2

Reaction notes

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