Allyl bromide → HCID 67437349, compound

HRID 500611Notes

Reaction equation

HRID 500611 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:5]([OH:6])=[CH:4][C:3]=1[OH:10].[CH2:11](Br)[CH:12]=[CH2:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:13]([O:6][C:5]1[C:7]([Cl:9])=[CH:8][C:2]([Cl:1])=[C:3]([OH:10])[CH:4]=1)[CH:12]=[CH2:11]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 672994,6-Dichloro-1,3-benzenediol

Product 1

HCID 67437349HCID 67437349, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,6-dichlororesorcinol (3.80 g, 21 mmol), allyl bromide (1.82 mL, 21 mmol) and potassium carbonate (2.24 g, 21 mmol) were combined in DMF and stirred at room temperature for 18 hours. The DMF was removed in vacuo and the residue acidified with 2M hydrochloric acid (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic solution was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with pentane:ethyl acetate 9:1 to 4:1 to afford the title compound as a yellow oil in 27% yield, 1.24 g.

Workup

  1. customThe DMF was removed in vacuo
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic solution was dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with pentane:ethyl acetate 9:1 to 4:1

Sources & evidence

ORD record
ord-0f1d3d6265864444b5bd7492284b0a04
Source dataset
uspto-grants-2010_08
Patent number
US07772223B2

Reaction notes

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