Chloroform → 2,2-Dimethylpropyl 3-bromobenzene-1-sulfonate

HRID 238351Notes

Reaction equation

HRID 238351 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].C(Cl)(Cl)Cl.[Br:11][C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])O.[Na+]>O.N1C=CC=CC=1>[Br:11][C:12]1[CH:13]=[C:14]([S:18]([O:4][CH2:3][C:2]([CH3:6])([CH3:5])[CH3:1])(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6404Neopentyl alcoholHCID 17943m-Bromobenzenesulphonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 574688212,2-Dimethylpropyl 3-bromobenzene-1-sulfonateYield 108.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Under cooling in an ice bath, 2,2-dimethyl-1-propanol (1.55 g) was added to a chloroform (20 mL) solution that contained 3-bromobenzenesulfonyl chloride (3.00 g) and pyridine (1.86 g), and the obtained solution was then stirred at a room temperature for 60 hours. Thereafter, water and a saturated sodium hydrogencarbonate aqueous solution were added to the reaction solution, and the obtained mixture was then extracted with chloroform. The organic layer was washed with a saturated saline, and was then dried over anhydrous sodium sulfate, followed by vacuum concentration. The obtained solid was washed with n-hexane, so as to obtain the title compound (3.90 g) in the form of a colorless solid.

Workup

  1. temperatureUnder cooling in an ice bath
  2. extractionthe obtained mixture was then extracted with chloroform
  3. washThe organic layer was washed with a saturated saline
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. concentrationfollowed by vacuum concentration
  6. washThe obtained solid was washed with n-hexane

Sources & evidence

ORD record
ord-88f24a232b204777bb7f02ac8d456237
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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