Triethylamine → Ethanol, 2-[(4-fluorophenyl)methoxy]-, 1-methanesulfonate

HRID 1992392Notes

Reaction equation

HRID 1992392 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][O:7][CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][CH2:8][CH2:9][O:10][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12192386HCID 12192386, compound

Product 1

HCID 18623184Ethanol, 2-[(4-fluorophenyl)methoxy]-, 1-methanesulfonateYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of 2-(4-fluorobenzyloxy)-ethanol (5.11 g, 30.0 mmol, from step (i) above) in methylene chloride (60 mL) was cooled to −10° C. Triethylamine (5.0 mL, 36 mmol) was added followed by methanesulfonyl chloride (3.78 g, 33.0 mmol) and the reaction mixture was stirred at −5° C. for 2 h. The reaction mixture was diluted with methylene chloride (200 mL) and the organic phase was washed with water (2×75 mL) and brine (75 mL), dried over MgSO4, and concentrated in vacuo to give 7.16 g (96%) of the title compound as a yellow oil.

Workup

  1. washthe organic phase was washed with water (2×75 mL) and brine (75 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58e59b1e021b4545bc742faffb04eba8
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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