Pyridine → (R)-2-butanol 4-bromobenzenesulfonate

HRID 1699345Notes

Reaction equation

HRID 1699345 reaction equation
[CH3:1][C@@H:2]([OH:5])[CH2:3][CH3:4].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.N1C=CC=CC=1.ClCCl>CN(C)C1C=CN=CC=1.O>[CH3:1][C@@H:2]([OH:5])[CH2:3][CH3:4].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O-:15])(=[O:5])=[O:14])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7396p-Bromobenzenesulfonyl chlorideHCID 84682(-)-2-Butanol

Product 1

HCID 131721473(R)-2-butanol 4-bromobenzenesulfonateYield 67%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 8.2 g of (R)-(−)2-butanol, 31.5 g of 1-bromo-4-benzenesulfonyl chloride, 1.0 g of N,N-dimethyl-4-pyridinamine, 55.5 ml of pyridine and 293 ml of dichloromethane was stirred for 3 days at room temperature. After the addition of water, stirring was continued for 1 hour. The reaction mixture was washed twice with a diluted hydrochloric acid solution and once with water, dried, filtered and evaporated in vacuo. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated, yielding 11.5 g (35.6%) of (R)-2-butanol 4-bromobenzenesulfonate (ester) (interm. 3).

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. washThe reaction mixture was washed twice with a diluted hydrochloric acid solution and once with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography over silica gel
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated

Sources & evidence

ORD record
ord-0512fbf6610d414f8e1651e950ebc7f4
Source dataset
uspto-grants-2002_02
Patent number
US06346518B1

Reaction notes

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