(Diethylamino)sulfur trifluoride → Diethyl fluoro(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylphosphonate

HRID 1666487Notes

Reaction equation

HRID 1666487 reaction equation
O[CH:2]([P:20](=[O:27])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)[CH:4]=1.CCN(S(F)(F)[F:34])CC>C(Cl)Cl>[F:34][CH:2]([P:20](=[O:27])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluoride2×HCID 86623917Diethyl hydroxy(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylphosphonate

Product 1

HCID 86623918Diethyl fluoro(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylphosphonateYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl hydroxy(3-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methylphosphonate (1.3 g, 3.2 mmol) in dry CH2Cl2 at −78° C. was added DAST (0.3 mL, 3.82 mmol) dropwise very slowly. The reaction mixture was allowed to reach RT, and stirred for 2 h. After completion of the reaction, excess DAST was quenched with water at 0° C. The mixture was extracted with CH2Cl2, dried and concentrated to dryness, and the residue was purified by column chromatography to give the pure title compound (940 mg). 1H NMR (500 MHz, CDCl3): δ 1.2 (m, 6H), 4.1 (m, 4H), 5.7 (dd, 1H, J=45 Hz, 5 Hz), 7.0 (d, 1H, J=10 Hz), 7.1 (d, 1H, J=5 Hz), 7.2-7.4 (m, 4H), 7.9 (m, 1H), 8.4 (s, 1H).

Workup

  1. customto reach RT
  2. customwas quenched with water at 0° C
  3. extractionThe mixture was extracted with CH2Cl2
  4. customdried
  5. concentrationconcentrated to dryness
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d73d6895b2204af2bff104d8a4d6cdff
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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