Ammonium Chloride → HCID 59750758, compound

HRID 748705Notes

Reaction equation

HRID 748705 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.Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].[Cl-].[NH4+]>CCCCCC.C(OCC)(=O)C.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:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 59750758HCID 59750758, compound

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Under an argon atmosphere and at −78° C., n-butyl lithium (a 1.57M hexane solution, 7.01 ml) was added dropwise 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. Then, the reaction mixture was cooled to −78° C. After the addition of t-butyl bromoacetate (1.48 ml, 10.0 mmol), the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was added with a saturated aqueous ammonium chloride solution, followed by extraction with diethyl ether. The extracts were combined, washed successively with water and brine, dried over MgSO4, and then distilled to remove the solvent. The residue thus obtained was subjected to chromatography on a short silica gel column (hexane-ethyl acetate 3:1). The solid thus obtained was recrystallized from hexane, whereby the title compound (3.30 g, 79%) was obtained as a colorless solid.

Workup

  1. temperatureThen, the reaction mixture was cooled to −78° C
  2. extractionfollowed by extraction with diethyl ether
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue thus obtained
  8. customThe solid thus obtained
  9. customwas recrystallized from hexane, whereby the title compound (3.30 g, 79%)
  10. customwas obtained as a colorless solid

Sources & evidence

ORD record
ord-d9c49e2f722243f98295f7ed0b81d6f8
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

Loading…