Sodium Chloride → (3-Chloro-4-fluorophenyl)methyl 4-methylbenzene-1-sulfonate

HRID 1034303Notes

Reaction equation

HRID 1034303 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[F:12])[CH2:7][OH:8].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.[Na+].[Cl-]>C1COCC1>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O:8][CH2:7][C:6]2[CH:9]=[CH:10][C:11]([F:12])=[C:4]([Cl:3])[CH:5]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 27736073-Chloro-4-fluorobenzyl alcohol

Product 1

HCID 54176025(3-Chloro-4-fluorophenyl)methyl 4-methylbenzene-1-sulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.33 g) was added to a solution of the alcohol from Step 3 (2.0 g) in THF (50 mL) at 0° C. under N2. Stirring was continued for 5 minutes at 0° C. followed by 25 min at 25° C. The mixture was then cooled to 0° C. and p-toluenesulfonyl chloride (2.5 g) was added. Stirring was continued for 40 minutes at 0° C. followed by 2 hours at 25° C. The precipitated NaCl was allowed to settle and the supernatant solution (4.0 mL) of the title compound was used directly in the next step.

Workup

  1. waitfollowed by 25 min at 25° C
  2. stirringStirring
  3. waitwas continued for 40 minutes at 0° C.
  4. waitfollowed by 2 hours at 25° C

Sources & evidence

ORD record
ord-00d1cc89f75144c587061d77c9751a8c
Source dataset
uspto-grants-1994_05
Patent number
US05314900

Reaction notes

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