Toluene → HCID 42634854, compound

HRID 1893118Notes

Reaction equation

HRID 1893118 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C1(C)C=CC=CC=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>O>[CH3:24][S:25]([O:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1230512,4-Difluorophenol

Product 1

HCID 42634854HCID 42634854, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

10.00 g (0.077 mol) of 2,4-difluorophenol, 100 mL of toluene and 8.17 g (0.081 mol) of triethylamine were mixed at 25° C., and with controlling the temperature of the reaction liquid to be at 20° C. or lower in an ice bath, 9.24 g (0.081 mol) of methanesulfonyl chloride was dropwise added thereto, taking 15 minutes, and these were reacted with stirring at 25° C. for 1 hour. Water was added to the reaction liquid to separate the organic layer, and the organic layer was washed twice with saturated sodium bicarbonate water and once with water, then dried with anhydrous MgSO4 and subjected to distillation under reduced pressure (98° C./3 Torr) to give 15.1 g of 2,4-difluorophenyl methanesulfonate (yield 94%).

Workup

  1. customthe temperature of the reaction liquid
  2. customto be at 20° C. or lower in an ice bath
  3. customthese were reacted
  4. customto separate the organic layer
  5. washthe organic layer was washed twice with saturated sodium bicarbonate water and once with water
  6. dry with materialdried with anhydrous MgSO4
  7. distillationsubjected to distillation under reduced pressure (98° C./3 Torr)

Sources & evidence

ORD record
ord-460ea55864e449ea942751d6549ace34
Source dataset
uspto-grants-2013_08
Patent number
US08512897B2

Reaction notes

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