Methanesulfonyl chloride → 4-Bromo-2,6-difluorobenzyl methanesulfonate

HRID 1360689Notes

Reaction equation

HRID 1360689 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH2:9][OH:10])=[C:4]([F:11])[CH:3]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C(Cl)Cl>[CH3:12][S:13]([O:10][CH2:9][C:5]1[C:4]([F:11])=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[F:8])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 27733034-Bromo-2,6-difluorobenzyl alcohol

Product 1

HCID 600525854-Bromo-2,6-difluorobenzyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4-bromo-2,6-difluorophenyl)methanol (24.8 g, 112.1 mmol) in CH2Cl2 (400 mL) was added TEA (22.68 g, 224.28 mmol) and methylsulfonyl chloride (12.84 mL, 156.9 mmol) at 0° C. The reaction was stirred at 0° C. for 1 h, quenched with aqueous NH4Cl, and diluted with EtOAc. The organic layer was washed with 1N HCl (2×), H2O, brine, dried over MgSO4, and condensed to give the desired compound.

Workup

  1. customquenched with aqueous NH4Cl
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with 1N HCl (2×), H2O, brine
  4. dry with materialdried over MgSO4, and condensed

Sources & evidence

ORD record
ord-c7d03034b712450cafc3514b40d463f1
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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