Allyl bromide → HCID 19594760, compound

HRID 612619Notes

Reaction equation

HRID 612619 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([OH:16])[CH:12]=[CH:13][C:14]=1[Br:15].[CH2:17](Br)[CH:18]=[CH2:19]>>[Br:15][C:14]1[CH:13]=[CH:12][C:11]([O:16][CH2:19][CH:18]=[CH2:17])=[CH:10][C:9]=1[O:8][CH3:7]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 3479554-Bromo-3-methoxyphenol

Product 1

HCID 19594760HCID 19594760, compound

Procedure

To a stirred mixture of K2CO3 (3.45 g, 0.025 mol), and 3-methoxy-4-bromo-phenol (6.09 g, 0.030 mol) at ambient temperature under argon is added allyl bromide (3.60 g, 0.030 mol). The resulting mixture is heated and stirred overnight. The mixture is filtered and the filtrate is concentrated on the rotovap. The residue is partitioned between Et2O and H2O. The Et2O layer is separated and extracted with 2×70 ml 5% NaOH, washed with brine, dried (MgSO4) and filtered. Evaporation on the rotovap followed by flash chromatography (EtOAc-hexane 1:9) gives 5.93 (81%) of the title compound. Rf-0.41 (EtOAc-hexane 25:75) HNMR (CDCl3) d 7.38 (d, 1H), 6.38 (dd, 1H) 6.1-5.9 (m, 1H), 5.41 (d, 1H), 5.29 (d, 1H), 4.51-4.48 (m, 2H), 3.84 (s, 3H).

Workup

  1. temperatureThe resulting mixture is heated
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate is concentrated on the rotovap
  4. customThe residue is partitioned between Et2O and H2O
  5. customThe Et2O layer is separated
  6. extractionextracted with 2×70 ml 5% NaOH
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customEvaporation on the rotovap

Sources & evidence

ORD record
ord-fd12c7e8cf464c7aa6f0df47d17e4629
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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