p-Bromobenzenesulfonyl chloride → 2-Adamantylethyl 4-bromobenzenesulfonate

HRID 1826477Notes

Reaction equation

HRID 1826477 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 aqueous hydrochloric acid (2M, 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-7d2d3c0f817942a6bf3a51df37a38c65
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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