Benzyl Bromide → HCID 59750798, compound

HRID 748764Notes

Reaction equation

HRID 748764 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.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(OCC)(=O)C.CCCCCC.CCCCCC.O.C(COC)OC>[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])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

8

Reactant 3

HCID 7498Benzyl BromideHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 59750798HCID 59750798, compoundYield 48%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8058HexaneSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Under an argon atmosphere and at −78° C., n-butyl lithium (a 1.60 M hexane solution, 459 μl, 0.734 mmol) was added to a dimethoxyethane solution (50 ml) of the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (202 mg, 0.667 mmol) obtained in Example 5. The temperature of the resulting mxiture was then elevated to room temperature. After the reaction mixture was cooled to −78° C., benzylbromide (87.2 μl, 0.734 mmol) was added dropwise thereto. While elevating the temperature of the reaction mixture to room temperature, stirring was conducted for 15 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The extracts were combined, washed with brine, dried over magnesium sulfate and then, concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=6:1 eluate was concentrated. The solid thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (125 mg, 0.318 mmol, 48%) was obtained as colorless needle crystals.

Workup

  1. customwas then elevated to room temperature
  2. customto room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue thus obtained
  8. concentrationethyl acetate=6:1 eluate was concentrated
  9. customThe solid thus obtained

Sources & evidence

ORD record
ord-1d46c2e110fe40b3bc0f507bf13afc85
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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