Water → HCID 11086667, compound

HRID 1663592Notes

Reaction equation

HRID 1663592 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19].O>C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC>[CH3:17][S:18]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:20])=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 11086667HCID 11086667, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of 4-bromobenzylalcohol (9.98 g) and triethylamine (11.2 μL) in ethyl acetate (100 mL) was added dropwise methanesulfonyl chloride (7.35 g) under nitrogen gas atmosphere and ice-cooling and the mixture was stirred under ice-cooling for 1 hour. To the reaction mixture was added water and the mixture was extracted with ethyl acetate (×2). After washing successively with water and a saturated brine, the organic layer was dried over anhydrous magnesium sulfate. After evaporation to remove solvent, the resultant crude product was triturated in ethyl acetate/hexane to 4-bromobenzyl methanesulfonate (13.54 g, yield: 91%) as crystals.

Workup

  1. temperatureice-cooling
  2. temperaturecooling for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate (×2)
  4. washAfter washing successively with water
  5. dry with materiala saturated brine, the organic layer was dried over anhydrous magnesium sulfate
  6. customAfter evaporation
  7. customto remove solvent

Sources & evidence

ORD record
ord-85df27ebcfe94ef6b762884962e87f6b
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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