(Diethylamino)sulfur trifluoride → HCID 59164426, compound

HRID 906612Notes

Reaction equation

HRID 906612 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10](O)[CH3:11])=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14].CCN(S(F)(F)[F:23])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([F:23])[CH3:11])=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 59164419HCID 59164419, compound

Product 1

HCID 59164426HCID 59164426, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-50 °C

Procedure

To a solution of 4-(1-hydroxy-ethyl)-2-nitro-benzoic acid methyl ester (1.09 g, 4.84 mmol) in DCM (15 mL) cooled at −50° C. was added dropwise a solution of DAST (0.734 mL, 5.32 mmol) in DCM (2 mL). The reaction was stirred at −50° C. for 2 h. Sat. aq NaHCO3 was added to reaction mixture and the solution was stirred at r.t. for 1 h. The aqueous phase was extracted with DCM (3×) and the combined organic phases were dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by flash chromatography (silica gel, hexanes to EtOAc/hexanes (4:6)) to give 4-(1-fluoro-ethyl)-2-nitro-benzoic acid methyl ester (0.60 g, 2.64 mmol, 56%). 1H-NMR (CDCl3, 300 MHz) 7.85 (s, 1H); 7.75 (d, J=7.9 Hz, 1H); 7.7.61 (d, J=7.3 Hz, 1H); 5.60-5.82 (qd, J=6.45, 47.2 Hz, 1H); 3.92 (s, 3H); 1.70 (dd, J=6.4, 23.7 Hz, 3H).

Workup

  1. stirringthe solution was stirred at r.t. for 1 h
  2. extractionThe aqueous phase was extracted with DCM (3×)
  3. dry with materialthe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash chromatography (silica gel, hexanes to EtOAc/hexanes (4:6))

Sources & evidence

ORD record
ord-4465560d1d2e4c6c9402350a78abbc4d
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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