Hydrogen Bromide → Bromomethyl tricyclo[3.3.1.13,7]dec-1-yl ketone

HRID 2294641Notes

Reaction equation

HRID 2294641 reaction equation
[C:1]12([C:11](Cl)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[BrH:14].[CH3:15]COC(C)=O>>[Br:14][CH2:15][C:11]([C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)=[O:12]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 989151-Adamantanecarbonyl chloride

Product 1

HCID 197820Bromomethyl tricyclo[3.3.1.13,7]dec-1-yl ketoneYield 60%

Procedure

This was prepared following the method of Example 3A. The intermediate diazoketone was prepared from 1-adamantane carboxylic acid chloride (2.98 g, 15 mmol) and CH2N2 (generated from Diazald® 8.7 g, 40 mmol) and subsequently treated with a saturated solution of HBr in EtOAc. Flash chromatography on silica gel (eluant EtOAc:hexane fr 8:92) afforded the title compound as a pale brown mobile oil (2.30 g, 60%).

Workup

  1. customThis was prepared

Sources & evidence

ORD record
ord-d5ed3019259542d8b2702d9679fde5f4
Source dataset
uspto-grants-1997_11
Patent number
US05688943

Reaction notes

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