1,3-Dibromopropane → 9-chloro-3,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehyde

HRID 1024485

Reaction equation

HRID 1024485 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6].Br[CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[C:9]2[O:10][CH2:13][CH2:14][CH2:15][O:11][C:8]=2[CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 24681823-Chloro-4,5-dihydroxybenzaldehyde

Product 1

HCID 49622469-chloro-3,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-chloro-4,5-dihydroxy benzaldehyde (4.15 g), of 1,3-dibromopropane (4.71 g, 0.92 eq.) and potassium carbonate (8.28 g, 2.5 eq.) in acetonitrile (160 ml) was heated to 60° C. overnight. The mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica (20% ethyl acetate in hexanes) to give the product as a white crystal. MS (m+1)=212.1

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5ea4580f0c9f4e5a95641458ceba33f3
Source dataset
uspto-grants-2014_05
Patent number
US08722896B2

Linked notes

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