Hydrogen Bromide → HCID 80147526, compound

HRID 1963048Notes

Reaction equation

HRID 1963048 reaction equation
C[Si](C=[N+]=[N-])(C)C.[CH3:8]CCCCC.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[CH2:22][C:23](Cl)=[O:24].[BrH:26]>O.C(#N)C.C1COCC1>[Br:26][CH2:8][C:23](=[O:24])[CH2:22][C:16]1[C:17]([F:21])=[CH:18][CH:19]=[CH:20][C:15]=1[Cl:14]

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 217957352-Chloro-6-fluorobenzeneacetyl chloride

Product 1

HCID 80147526HCID 80147526, compoundYield 76.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 2 M solution of trimethylsilyl-diazomethane in hexane (6.54 ml, 13.07 mmol) cooled to 0° C. under argon was added dropwise a solution of 2-chloro-6-fluoro-phenylacetyl chloride (1.23 g, 5.94 mmol) in 24 ml of a mixture of THF and ACN (1:1). The mixture was stirred at 0° C. for 5 h. Then 48% aqueous hydrobromic acid (5.91 ml, 52.28 mmol) was added dropwise and the solution was stirred at room temperature overnight. Then 40 ml of water were added. The aqueous phase was extracted twice with EA, and the combined organic phases were washed with water, a saturated solution of sodium hydrogencarbonate and brine, dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0, then 95:5) to give 1.20 g of the title compound as a white powder having a melting point of 47° C.

Workup

  1. stirringthe solution was stirred at room temperature overnight
  2. extractionThe aqueous phase was extracted twice with EA
  3. washthe combined organic phases were washed with water
  4. dry with materiala saturated solution of sodium hydrogencarbonate and brine, dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0

Sources & evidence

ORD record
ord-1577596bd8a94949ba14809710d59ec3
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

Loading…