Hexane → HCID 59750739, compound

HRID 748702Notes

Reaction equation

HRID 748702 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.Br[CH2:32][CH2:33][O:34][CH2:35][CH2:36]Br>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:12]3[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=3[F:19])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 21521Bis(2-bromoethyl) etherHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 59750739HCID 59750739, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (1.0 g, 3.30 mmol) obtained in Example 5 was dissolved in tetrahydrofuran (70 ml). At −78° C., a hexane solution (1.57M, 5.3 ml, 8.3 mmol) of n-butyl lithium was added dropwise. After completion of the dropwise addition, the reaction mixture was stirred at −78° C. for 10 minutes and then stirred for another 30 minutes under ice cooling. At −78° C., 2-bromoethyl ether (0.55 ml, 3.9 mmol) was added dropwise to the reaction mixture. After completion of the dropwise addition, the temperature of the reaction mixture was elevated to room temperature over 14 hours. Water (2.0 ml) was added to the reaction mixture. The residue obtained by concentrating the resulting mixture under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=5:1) to yield a white solid. The resulting white solid was washed with diisopropyl ether/methylene chloride, whereby the title compound (317 mg, 26%) was obtained as a white powder.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringstirred for another 30 minutes under ice cooling
  3. additionAfter completion of the dropwise addition
  4. waitthe temperature of the reaction mixture was elevated to room temperature over 14 hours
  5. customThe residue obtained
  6. concentrationby concentrating the resulting mixture under reduced pressure
  7. customwas purified by silica gel chromatography (hexane:ethyl acetate=5:1)
  8. customto yield a white solid
  9. washThe resulting white solid was washed with diisopropyl ether/methylene chloride, whereby the title compound (317 mg, 26%)
  10. customwas obtained as a white powder

Sources & evidence

ORD record
ord-68588990d4e24b009f649277b4f03688
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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