Potassium Carbonate → 2-(2,2-Dibromovinyl)-5-methylphenol

HRID 1773213Notes

Reaction equation

HRID 1773213 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[CH:12]=[C:13]([Br:15])[Br:14])(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[Br:14][C:13]([Br:15])=[CH:12][C:6]1[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=1[OH:4]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 1184524502-(2,2-Dibromovinyl)-5-methylphenyl acetate

Product 1

HCID 1184526172-(2,2-Dibromovinyl)-5-methylphenolYield 93.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-(2,2-dibromovinyl)-5-methylphenyl acetate (16.5 g, 49.4 mmol) in 100 mL of MeOH was treated with a solution of K2CO3 (10.24 g, 74.1 mmol) dissolved in 5.0 mL of water and stirred at RT. The reaction mixture immediately turned yellow and cloudy. After 30 min the mixture was concentrated under reduced pressure to remove MeOH. The crude material was diluted with water and carefully adjusted to pH˜5-6 via addition of 2M HCl. The crude mixture was extracted with EtOAc×2, dried over MgSO4, filtered, and concentrated under reduced pressure to give an orange oil, 2-(2,2-dibromovinyl)-5-methylphenol (13.5 g). 1H NMR (400 MHz, DMSO-d6) δ 2.21 (s, 3H), 6.65 (d, J=8.2 Hz, 1H), 6.68 (s, 1H), 7.49 (d, J=7.9 Hz, 1H), 7.57 (s, 1H), 9.83 (s, 1H).

Workup

  1. concentrationAfter 30 min the mixture was concentrated under reduced pressure
  2. customto remove MeOH
  3. additionThe crude material was diluted with water
  4. additioncarefully adjusted to pH˜5-6 via addition of 2M HCl
  5. extractionThe crude mixture was extracted with EtOAc×2
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70f4aa10bbe44656b3f3a6789730dd45
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Reaction notes

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