Ethanol → 5-Bromo-2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran

HRID 1155953Notes

Reaction equation

HRID 1155953 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([OH:10])[C:7]([CH3:12])([CH3:11])[C:6]=2[CH:13]=1.[CH2:14](O)[CH3:15]>S(=O)(=O)(O)O.C(N(CC)CC)C.CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([O:10][CH2:14][CH3:15])[C:7]([CH3:11])([CH3:12])[C:6]=2[CH:13]=1

Participants

6

Reactant 2

HCID 702EthanolHCID 205362245-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran

Product 1

HCID 205362435-Bromo-2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuranYield 86%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 8471TriethylamineCatalystHCID 3283Diethyl EtherSolvent

Procedure

5-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran (5 g, 0.02 mole) was heated under reflux in ethanol (30 ml) with sulphuric acid (4 drops) for 11/2 hours. The solution was cooled, neutralised with a few drops of triethylamine and run down. The residue was redissolved in ether and the solution washed with water, dried over magnesium sulphate and the solvent removed under vacuum leaving 4.7 g (86%) title product as a buff-coloured oil. The structure was confirmed by NMR.

Workup

  1. temperatureThe solution was cooled
  2. washthe solution washed with water
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-443ac085b26b4b78b252e86cb0ade00b
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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