1-Acetoxy-2-bromoethane → Ethyl 3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propionate

HRID 748681Notes

Reaction equation

HRID 748681 reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])(=[O:15])=[O:14])=[CH:9][CH:8]=1.[C:25]([O:28][CH2:29][CH2:30]Br)(=[O:27])[CH3:26].[Cl-].[NH4+]>C(COC)OC.CCCCCC>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH:16]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[CH2:26][C:25]([O:28][CH2:29][CH3:30])=[O:27])(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 135641-Acetoxy-2-bromoethaneHCID 25517Ammonium ChlorideHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 59750785Ethyl 3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propionate

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Under an argon atmosphere and at −78° C., n-butyl lithium (a 1.57M hexane solution, 7.01 ml) was added to a dimethoxyethane solution (50 ml) of the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (3.03 g, 10.0 mmol) obtained in Example 5. The temperature of the reaction mixture was raised to room temperature, at which stirring was conducted for 15 minutes. After cooling to −78° C., bromoethyl acetate (1.33 ml, 12.0 mmol) was added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. To the reaction mixture was added a saturated ammonium chloride solution, followed by extraction with diethyl ether. The extracts were combined, washed successively with water, a saturated aqueous solution of sodium thiosulfate, and brine, dried over MgSO41 and then distilled under reduced pressure to remove the solvent. The residue thus obtained was recrystallized from hexane, whereby the title compound (1.95 g, 50%) was obtained as colorless needle crystals.

Workup

  1. temperatureAfter cooling to −78° C.
  2. stirringThe mixture was stirred at room temperature for 3 hours
  3. extractionfollowed by extraction with diethyl ether
  4. washwashed successively with water
  5. dry with materiala saturated aqueous solution of sodium thiosulfate, and brine, dried over MgSO41
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue thus obtained
  9. customwas recrystallized from hexane, whereby the title compound (1.95 g, 50%)
  10. customwas obtained as colorless needle crystals

Sources & evidence

ORD record
ord-c2f0ff6662fa40dd8475263b60a56d83
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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