3-Bromobenzaldehyde → HCID 10847790, compound

HRID 1391741Notes

Reaction equation

HRID 1391741 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(=O)=O.CC(C)=O.[CH2:17]([Mg]Cl)[CH2:18][CH2:19][CH3:20]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH2:17][CH2:18][CH2:19][CH3:20])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 765833-BromobenzaldehydeHCID 18522661Acetone cardiceHCID 178418265HCID 178418265, compound

Product 1

HCID 10847790HCID 10847790, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To 3-bromobenzaldehyde (5.00 g, 27.02 mmol) in dry THF (100 mL), under nitrogen at −78° C. (dry ice/acetone bath) was added nBuMgCl (16.2 mL of a 2.0M solution in THF, 0.032 mol) and the reaction stirred for 1 hour at −78° C. and then allowed to warm to rt overnight. The reaction was then quenched with water, extracted with EtOAc and the layers separated. The organic layer was washed with water then brine, dried (Na2SO4) and reduced under vacuum to give a colourless oil. Purification by Biotage™ chromatography (silica, 90 g cartridge) eluting with cyclohexane:EtOAc 9:1 afforded the title compound as a colourless oil (4.07 g).

Workup

  1. temperatureto warm to rt overnight
  2. customThe reaction was then quenched with water
  3. extractionextracted with EtOAc
  4. customthe layers separated
  5. washThe organic layer was washed with water
  6. dry with materialbrine, dried (Na2SO4)
  7. customto give a colourless oil
  8. customPurification by Biotage™ chromatography (silica, 90 g cartridge)
  9. washeluting with cyclohexane:EtOAc 9:1

Sources & evidence

ORD record
ord-af067f498b0c4051a8570b3e3e702625
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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