Sodium Iodide → Benzene, 4-bromo-2-[(4,4-difluoro-3-buten-1-yl)oxy]-1-fluoro-

HRID 30593

Reaction equation

HRID 30593 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:19][CH2:20][CH:21]=[C:22]([F:24])[F:23]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(C(C)=O)C.ClCCl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:9][CH2:19][CH2:20][CH:21]=[C:22]([F:24])[F:23])[CH:4]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 183421Phenol, 5-bromo-2-fluoro-HCID 27822404-Bromo-1,1-difluorobut-1-ene

Product 1

HCID 59790300Benzene, 4-bromo-2-[(4,4-difluoro-3-buten-1-yl)oxy]-1-fluoro-Yield 63%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-fluoro-5-bromophenol (2.40 g), potassium carbonate (2.31 m), Aliquat 336 (5 drops), sodium iodide (catalytic) and 4-bromo-1,1-difluoro-1-butene (1.79 mL) in methyl ethyl ketone was placed in a pressure vessel and heated in a 82° oil bath for 15 hours. The reaction mixture was cooled, diluted with dichloromethane, filtered and evaporated in vacuo. The resultant residue was purified by flash chromatography (silica gel, eluant: 2.5% ethyl acetate/hexane to afford 4-bromo-2-(4,4-difluorobut-3-enyloxy)-1-fluorobenzene, 2.23 g (63% yield), identified by NMR analysis.

Workup

  1. customwas placed in a pressure vessel
  2. temperatureheated in a 82° oil bath for 15 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe resultant residue was purified by flash chromatography (silica gel, eluant

Sources & evidence

ORD record
ord-64e03f43ee504125a8fbde98ebe10950
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Linked notes

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