p-Bromobenzenesulfonyl chloride → 2-Adamantylethyl 4-bromobenzenesulfonate

HRID 397727Notes

Reaction equation

HRID 397727 reaction equation
[C:1]12([CH:11]([OH:13])C)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)C1)[CH2:8]2.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(N([CH2:30][CH3:31])CC)C>ClCCl.Cl>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([O:13][CH2:11][CH2:1][CH:10]2[CH:5]3[CH2:6][CH:7]4[CH2:9][CH:3]([CH2:30][CH:31]2[CH2:8]4)[CH2:4]3)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 27697131-(1-Adamantyl)ethanol

Product 1

HCID 544780962-Adamantylethyl 4-bromobenzenesulfonateYield 88%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-adamantylethanol (5.8 g, 32 mmol) in triethylamine (6.7 ml) and dichloromethane (50 ml) was added 4-bromobenzenesulphonyl chloride (8.9 g, 35 mmol) at room temperature. The solution was stirred for 16 h, diluted with 2N aqueous hydrochloric acid (100 ml) and extracted with dichloromethane (100 ml). The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) and brine (100 ml), dried (MgSO4), and concentrated in vacuo to give the title compound as a white crystalline solid (11.2 g, 88%).

Workup

  1. extractionextracted with dichloromethane (100 ml)
  2. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) and brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c3262c87eba4414fbd45e1a5684d329c
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

Loading…