(Diethylamino)sulfur trifluoride → 2-Bromo-4-(1-fluorocyclopropyl)-1-methoxybenzene

HRID 406397Notes

Reaction equation

HRID 406397 reaction equation
C(N(S(F)(F)[F:7])CC)C.[Br:10][C:11]1[CH:12]=[C:13]([C:19]2(O[Si](C)(C)C)[CH2:21][CH2:20]2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]>ClCCl.O>[Br:10][C:11]1[CH:12]=[C:13]([C:19]2([F:7])[CH2:21][CH2:20]2)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 66618984[1-(3-Bromo-4-methoxyphenyl)cyclopropyloxy]trimethylsilane

Product 1

HCID 666334672-Bromo-4-(1-fluorocyclopropyl)-1-methoxybenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Diethylaminosulfur trifluoride (2.4 ml) was added to a solution of [1-(3-bromo-4-methoxyphenyl)cyclopropyloxy]trimethylsilane (3.84 g) in dichloromethane (68 ml). The reaction mixture was stirred at room temperature for 2.5 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (1.88 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-726dfb4c1ab8487dba67ae08046d3264
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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