Ethyl Acetate → 1,1-dibromo-1,2-difluoro-2-(3-nitro-4-methoxy-phenyl)ethane

HRID 2100250Notes

Reaction equation

HRID 2100250 reaction equation
CCN(S(F)(F)[F:7])CC.[Br:10][C:11]([Br:26])([F:25])[CH:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=1)O.CCOC(C)=O>C(Cl)Cl>[Br:10][C:11]([Br:26])([F:25])[CH:12]([F:7])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 123472(Diethylamino)sulfur trifluorideHCID 12135311HCID 12135311, compound

Product 1

HCID 121353121,1-dibromo-1,2-difluoro-2-(3-nitro-4-methoxy-phenyl)ethane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(DAST 730 μL (5.58 mmol; 1.8 eq) in 5 mL CH2Cl2 was added to a solution of 1.146 g (3.1 mmol) of the alcohol (7) in 7 mL CH2Cl2 at −78° C. The reaction mixture was allowed to warm up to 0° C. over a period of 2 h, quenched with 15 mL of NaHCO3 saturated solution and diluted with 20 mL of diethyl ether. The organic phase was dried over anhydrous sodium sulfate and purified by chromatography on SiO2 using Hexane/Ethyl Acetate 7:3 to give 960 mg (2.6 mmol; 84%) of a yellow oil. Rf=0.493 (Hex./AcOEt 7:3)

Workup

  1. customquenched with 15 mL of NaHCO3 saturated solution
  2. additiondiluted with 20 mL of diethyl ether
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. custompurified by chromatography on SiO2
  5. customto give 960 mg (2.6 mmol; 84%) of a yellow oil

Sources & evidence

ORD record
ord-19ec94e11f5141bfb3c85a810b89c8da
Source dataset
uspto-grants-2009_08
Patent number
US07572778B2

Reaction notes

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