Methanesulfonyl chloride → Methanesulfonic acid 3-chloro-1-phenyl-propyl ester

HRID 1869205Notes

Reaction equation

HRID 1869205 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH:4]([O:5][S:13]([CH3:12])(=[O:15])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 5720643-Chloro-1-phenylpropanol

Product 1

HCID 57985877Methanesulfonic acid 3-chloro-1-phenyl-propyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the 3-chloro-1-phenyl-propan-1-ol (1.5 g, 8.79 mmol) in DCM at 0° C. (50 mL) was added TEA (1.6 mL, 11.4 mmol) followed by MsCl (0.75 mL, 9.7 mmol). The reaction mixture was stirred 1.5 hours at 0° C., quenched with ice, and partitioned between a saturated solution of NaHCO3 and DCM. The organic layer was separated, washed with brine, dried over MgSO4, filtered, and concentrated at 0° C. The methanesulfonic acid 3-chloro-1-phenyl-propyl ester (95% crude yield, 2.08 g) thus prepared was used in the next step without purification.

Workup

  1. customquenched with ice
  2. custompartitioned between a saturated solution of NaHCO3 and DCM
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated at 0° C
  8. customThe methanesulfonic acid 3-chloro-1-phenyl-propyl ester (95% crude yield, 2.08 g) thus prepared
  9. customwas used in the next step without purification

Sources & evidence

ORD record
ord-1b8b2c5dbf29486ba74bc3a644092bb7
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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