Methanesulfonyl chloride → (2'-Chloro-3-methylbiphenyl-4-yl)methyl methanesulfonate

HRID 2194881Notes

Reaction equation

HRID 2194881 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[C:10]([CH3:16])[CH:9]=1.C(N(C(C)C)CC)(C)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl.O>[CH3:26][S:27]([O:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:9][C:10]=1[CH3:16])(=[O:29])=[O:28]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67448566(2'-Chloro-3-methylbiphenyl-4-yl)methanol

Product 1

HCID 86658848(2'-Chloro-3-methylbiphenyl-4-yl)methyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2′-chloro-3-methylbiphenyl-4-yl)methanol from step 1 in CH2Cl2 (0.13M) at 0° C. was added diisopropyl ethylamine (1.5 eq.) then methanesulfonyl chloride (1.1 eq.). The reaction mixture was stirred at room temperature for 2 h, poured in water and extracted with EtOAc. The organic extract was washed with water, brine, dried over MgSO4 filtered and concentrated to afford the title compound which was used as such in the next step.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4e3be230bca0449c922820128be7d0df
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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