Methanesulfonyl chloride → 3-Chloro-5-trifluoromethoxybenzyl mesylate

HRID 1717467Notes

Reaction equation

HRID 1717467 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:9]=1)[CH2:5][OH:6].CCN(C(C)C)C(C)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[S:25]([O:6][CH2:5][C:4]1[CH:7]=[C:8]([O:10][C:11]([F:12])([F:13])[F:14])[CH:9]=[C:2]([Cl:1])[CH:3]=1)(=[O:27])(=[O:26])[CH3:24]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 177507383-Chloro-5-(trifluoromethoxy)benzyl alcohol

Product 1

HCID 219046353-Chloro-5-trifluoromethoxybenzyl mesylateYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-chloro-5-trifluoromethoxybenzyl alcohol (6.1 g, 26.9 mmol; see Example 6(v) above) in CH2Cl2 (250 mL) at 0° C. under a nitrogen atmosphere was added DIPEA (4.2 g, 32.3 mmol) and methanesulfonyl chloride (3.4 g, 29.6 mmol). The solution was stirred at 0° C. for 1.5 hours and quenched with H2O. The organics were separated and then washed with H2O (1×), 1N HCl (1×), H2O (1×) and aqueous NaHCO3 (1×) and then dried (Na2SO4), filtered and concentrated to afford the sub-title compound (8.2 g, 99%) as an oil.

Workup

  1. customquenched with H2O
  2. customThe organics were separated
  3. washwashed with H2O (1×), 1N HCl (1×), H2O (1×) and aqueous NaHCO3 (1×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-de88f88e1b934fb1b2f03553ebc5622c
Source dataset
uspto-grants-2010_09
Patent number
US07803954B2

Reaction notes

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