p-Bromobenzenesulfonyl chloride → (tetrahydro-2H-pyran-2-yl)methyl 4-bromobenzenesulfonate

HRID 451748Notes

Reaction equation

HRID 451748 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8].CCN(CC)CC.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:8][CH2:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 7524Tetrahydropyran-2-methanolHCID 8471Triethylamine

Product 1

HCID 21813678(tetrahydro-2H-pyran-2-yl)methyl 4-bromobenzenesulfonateYield 70.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A CH2Cl2 solution of (tetrahydro-2H-pyran-2-yl)methanol (7.91 g, 68.1 mmol), Et3N (14 mL, 102 mmol), and catalytic DMAP was treated with 4-bromobenzenesulfonyl chloride (14.3 g, 74.9 mmol). After 2 h, the reaction was quenched with water. The organic layer was washed with 1M HCl and brine, dried over Na2SO4, filtered, and concentrated. The crude material was purified by chromatography on silica gel (EtOAc/Hex) to afford ((tetrahydro-2H-pyran-2-yl)methyl 4-bromobenzenesulfonate as an oil (16 g).

Workup

  1. customthe reaction was quenched with water
  2. washThe organic layer was washed with 1M HCl and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by chromatography on silica gel (EtOAc/Hex)

Sources & evidence

ORD record
ord-cf37d51bc73a40afaf68c94eb24508b1
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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