Chloroform → HCID 86677502, compound

HRID 1400660Notes

Reaction equation

HRID 1400660 reaction equation
[F:1][CH2:2][CH2:3][OH:4].[N+:5]([C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[S:17](Cl)(=[O:19])=[O:18])([O-:7])=[O:6].C(Cl)(Cl)Cl>N1C(C)=CC=CC=1C>[N+:5]([C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[S:17]([O:4][CH2:3][CH2:2][F:1])(=[O:19])=[O:18])([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 97372-FluoroethanolHCID 74255Benzenesulfonyl chloride, 2,4-dinitro-

Product 1

HCID 86677502HCID 86677502, compound

Reagents, catalysts & solvents 1

HCID 79372,6-LutidineSolvent

Procedure

To a solution of 2-fluoroethanol (1.28 g, 20 mmol) in 2,6-lutidine (20 mL) at −10° C. was added 2,4-dinitrobenzene-1-sulfonyl chloride LVI (4.91 g, 18.7 mmol) in portions. A precipitate formed so CHCl3 (50 mL) was added to the reaction mixture in order to ensure efficient stirring. After 10 min, the mixture was washed with cold 10% aqueous HCl (150 mL) and water (2×50 mL). The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (1:2 EtOAc:hexane) to afford 2-fluoroethyl 2,4-dinitrobenzenesulfonate LVII (1.44 g, 4.90 mmol, 24%).

Workup

  1. additionwas added to the reaction mixture in order
  2. washthe mixture was washed with cold 10% aqueous HCl (150 mL) and water (2×50 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel (1:2 EtOAc:hexane)

Sources & evidence

ORD record
ord-c51cc26d04d1465b8fa75946df707ad9
Source dataset
uspto-grants-2014_12
Patent number
US08906868B2

Reaction notes

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