(Diethylamino)sulfur trifluoride → HCID 118045958, compound

HRID 595982Notes

Reaction equation

HRID 595982 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9]O)[CH:5]=[C:6]([F:8])[CH:7]=1.CCN(S(F)(F)[F:17])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][F:17])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 2769402(3-Bromo-5-fluorophenyl)methanol

Product 1

HCID 118045958HCID 118045958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-bromo-5-fluorophenyl)methanol (4 g, 19.51 mmol) in DCM (39.0 mL) at 0° C., DAST (3.35 mL, 25.4 mmol) was added. The reaction mixture was allowed to return to room temperature and stirred at room temperature overnight. Sat. NaHCO3 was added, the reaction mixture was then extracted by DCM. The organic was dried and concentrated. The crude material was purified by flash chromatography (0-10% EtOAc/heptanes) to yield the final product as colorless oil. LCMS (m/z): no mass (MH+), 0.86 min. 1H NMR (400 MHz, CDCl3) δ ppm 7.30 (s, 1H), 7.23 (d, J=8.2 Hz, 1H), 7.03 (d, J=8.6 Hz, 1H), 5.41 (s, 1H), 5.29 (s, 1H).

Workup

  1. customto return to room temperature
  2. extractionthe reaction mixture was then extracted by DCM
  3. customThe organic was dried
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography (0-10% EtOAc/heptanes)

Sources & evidence

ORD record
ord-0fa81b63fb234348815c9ce3ec01e60e
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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