4-Toluenesulfonyl chloride → 3,3-Bis(4-fluorophenyl)propyl 4-methylbenzenesulfonate

HRID 2190304Notes

Reaction equation

HRID 2190304 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>N1C=CC=CC=1>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:11][CH2:10][CH2:9][CH:8]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 197832883,3-Bis(4-fluorophenyl)propanol

Product 1

HCID 222258963,3-Bis(4-fluorophenyl)propyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3,3-bis(4-fluorophenyl)propan-1-ol (4.99 g, 20.1 mmol) in pyridine (60 mL) at 0° C. was added 4-methylbenzene-1-sulfonyl chloride (4.20 g, 22.0 mmol). The reaction mixture was stirred at 0° C. for 4 h, warmed to room temperature and stirred for 4 h. The reaction mixture was partially concentrated, diluted with EtOAc, washed with 1 M HCl (2×), saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated to give 3,3-bis(4-fluorophenyl)propyl 4-methylbenzenesulfonate which was used in the next step without further purification.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 4 h
  3. concentrationThe reaction mixture was partially concentrated
  4. additiondiluted with EtOAc
  5. washwashed with 1 M HCl (2×), saturated NaHCO3 (1×), brine (1×)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-63da7dcf30b3492b906fddd5c9753499
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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