Methanol → 3-(3-Bromophenyl)pentanedial

HRID 2061610Notes

Reaction equation

HRID 2061610 reaction equation
[O:1]=[O+][O-].[Br:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH2:15][CH:16]=C)[CH2:12]C=C)[CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:37][OH:38]>C(Cl)Cl>[Br:4][C:5]1[CH:6]=[C:7]([CH:11]([CH2:15][CH:16]=[O:1])[CH2:12][CH:37]=[O:38])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 24823OzoneHCID 673089671-Bromo-3-(hepta-1,6-dien-4-yl)benzene

Product 1

HCID 866405263-(3-Bromophenyl)pentanedial

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Ozone was bubbled through a solution of 1-bromo-3-(hepta-1,6-dien-4-yl)benzene (6.14 g, 24.4 mmol) in CH3OH (10 ml) and CH2Cl2 (90 ml) at −78° C. for 30 min at which time the solution was pale blue. Nitrogen was then bubbled through the solution for 5 min and the solution became clear. Polymer support triphenylphosphine (20 g, 60.0 mmol) was added and the solution stirred at −78° C. for 30 min. The dry ice/acetone bath was removed and the heterogeneous mixture was stirred for 1 h. The heterogeneous mixture was filtered through Celite and the filtrate was concentrated to afford compound 87.

Workup

  1. customNitrogen was then bubbled through the solution for 5 min
  2. customThe dry ice/acetone bath was removed
  3. stirringthe heterogeneous mixture was stirred for 1 h
  4. filtrationThe heterogeneous mixture was filtered through Celite
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9dcfb46a6db743b8a5e059ceb8c92c6e
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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