Dimethylformamide → Bicyclo[2.2.1]heptane-7-carbaldehyde

HRID 1161355

Reaction equation

HRID 1161355 reaction equation
Br[CH:2]1[CH:6]2[CH2:7][CH2:8][CH:3]1[CH2:4][CH2:5]2.[Mg].CN([CH:13]=[O:14])C>C(OCC)C>[CH:6]12[CH:2]([CH:13]=[O:14])[CH:3]([CH2:8][CH2:7]1)[CH2:4][CH2:5]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 5653597-Bromobicyclo[2.2.1]heptaneHCID 5462224Magnesium

Product 1

HCID 84647822Bicyclo[2.2.1]heptane-7-carbaldehydeYield 48.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
2.5 °C

Procedure

15.9 g (81 mmol) of 7-Bromo-bicyclo[2.2.1]heptane were added dropwise to 2 g magnesium (81 mmol) in 25 ml of diethyl ether and refluxed for 2.5 h. The mixture was cooled to 0-5° C. and 6.3 ml (81 mmol) of DMF were added dropwise. The mixture was then refluxed for 2 h, cooled to room temperature and the white solid filtered off and washed with ether. The filtrate was reduced and 4.87 g of a white solid were obtained. The intermediate was used without further characterization.

Workup

  1. temperaturerefluxed for 2.5 h
  2. temperatureThe mixture was then refluxed for 2 h
  3. temperaturecooled to room temperature
  4. filtrationthe white solid filtered off
  5. washwashed with ether

Sources & evidence

ORD record
ord-3677f50506fc4935bf76f6977304ac04
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Linked notes

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