Toluene → HCID 18504640, compound

HRID 842565Notes

Reaction equation

HRID 842565 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>O>[CH3:30][S:31]([O:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:13])[F:14])=[CH:8][N:7]=1)(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 112067993-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}propan-1-ol

Product 1

HCID 18504640HCID 18504640, compoundYield 117.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.0 g of 2-(3-hydroxypropyloxy)-5-trifluoromethylpyridine, 3.4 ml of triethylamine and 25 ml of toluene was vigorously stirred under a nitrogen stream, while cooling in chilled water bath to 5° C. Then, 1.63 g of methanesulfonyl chloride was added dropwise to this mixture at such a rate that the reaction temperature did not exceed 10° C., and the chilled water bath was removed. After further stirring continued at room temperature for 1.5 hours, 250 ml of water was added thereto, and the mixture was vigorously stirred for further 30 minutes, followed by phase separation. The toluene layer was washed once with water, dried with magnesium sulfate, and concentrated, which afforded 5 g of 2-(3-methanesulfonyloxypropyloxy)-5-trifluoromethylpyridine as an oily product (92% yield).

Workup

  1. customdid not exceed 10° C.
  2. customthe chilled water bath was removed
  3. stirringAfter further stirring
  4. addition250 ml of water was added
  5. stirringthe mixture was vigorously stirred for further 30 minutes
  6. customfollowed by phase separation
  7. washThe toluene layer was washed once with water
  8. dry with materialdried with magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6f8932b03ec84f5e923b3e00b445090a
Source dataset
uspto-grants-2002_04
Patent number
US06376428B1

Reaction notes

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