(Diethylamino)sulfur trifluoride → 1-(3,5-Di-tert-butyl-4-hydroxyphenyl)-3-fluoro-3-methyl-butan-1-one

HRID 2260174Notes

Reaction equation

HRID 2260174 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16](=[O:22])[CH2:17][C:18](O)([CH3:20])[CH3:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:29])CC)C>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([C:16](=[O:22])[CH2:17][C:18]([F:29])([CH3:20])[CH3:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 99265721-(3,5-Di-tert-butyl-4-hydroxyphenyl)-3-hydroxy-3-methyl-butan-1-one

Product 1

HCID 190001861-(3,5-Di-tert-butyl-4-hydroxyphenyl)-3-fluoro-3-methyl-butan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-hydroxy-3-methyl-butan-1-one (2.5 g) in dry methylene chloride (30 mL) cooled to -78° C. is added diethylaminosulfur trifluoride (Aldrich Chemical Co.) (1.2 mL) and the stirring is continued for an additional 45 minutes. The mixture is washed with water and saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, and the solvent is removed under reduced pressure. The crude product is purified by silica gel column chromatography (hexane:ethyl acetate, 9:1) followed by crystallization from petroleum ether to give 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-fluoro-3-methyl-butan-1-one as a white solid, mp 94° C.

Workup

  1. washThe mixture is washed with water and saturated aqueous sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent is removed under reduced pressure
  4. customThe crude product is purified by silica gel column chromatography (hexane:ethyl acetate, 9:1)
  5. customfollowed by crystallization from petroleum ether

Sources & evidence

ORD record
ord-aa12eb822fab4848abf91505754f3da1
Source dataset
uspto-grants-1995_12
Patent number
US05476876

Reaction notes

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