Neopentyl alcohol → Neopentyl 4-bromobenzenesulfonate

HRID 732794Notes

Reaction equation

HRID 732794 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([OH:17])[C:13]([CH3:16])([CH3:15])[CH3:14]>N1C=CC=CC=1>[CH3:14][C:13]([CH3:16])([CH3:15])[CH2:12][O:17][S:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 6404Neopentyl alcoholHCID 7396p-Bromobenzenesulfonyl chloride

Product 1

HCID 2802228Neopentyl 4-bromobenzenesulfonateYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Add 4-bromobenzenesulfonyl chloride (2.20 g, 8.61 mmol) and pyridine (30 mL) to a round bottom flask. At ambient temperature, with stirring, add neopentyl alcohol (1.39 mL, 12.91 mmol). After stirring the reaction overnight at ambient temperature quench the reaction with saturated aqueous sodium bicarbonate and extract it with ethyl acetate. Wash the combined extracts with saturated aqueous sodium bicarbonate, 0.05 N aqueous hydrochloric acid and brine, then dry (sodium sulfate), and concentrate in vacuo. Purify the resulting material on a flash column (silica gel; 30%-50% gradient of CH2Cl2 in hexanes) to provide 2.24 g of 4-bromo-benzenesulfonic acid 2,2-dimethyl-propyl ester (85%).

Workup

  1. stirringAfter stirring
  2. customthe reaction overnight at ambient temperature
  3. customquench
  4. customthe reaction with saturated aqueous sodium bicarbonate
  5. extractionextract it with ethyl acetate
  6. washWash the combined extracts with saturated aqueous sodium bicarbonate, 0.05 N aqueous hydrochloric acid and brine
  7. dry with materialdry (sodium sulfate)
  8. concentrationconcentrate in vacuo
  9. customPurify the resulting material on a flash column (silica gel; 30%-50% gradient of CH2Cl2 in hexanes)

Sources & evidence

ORD record
ord-570927af829342aeacd463fb567226b5
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

Loading…