Allyl bromide → HCID 67437349, compound

HRID 2387669Notes

Reaction equation

HRID 2387669 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-7e1d4813ee5747f388239bc8975a2df8
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

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