Hydrochloric Acid → HCID 20536200, compound

HRID 1155959Notes

Reaction equation

HRID 1155959 reaction equation
Br[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.Cl.[CH3:15][N:16](C)C=O>O>[C:15]([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)#[N:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 205362245-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran

Product 1

HCID 20536200HCID 20536200, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Bromo-2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran (7.3 g), prepared as in Example 5(e) and cuprous cyanide (3.2 g) were heated under reflux in dimethylformamide (10 ml) with stirring for 51/2 hours. The mixture was cooled to room temperature and a solution of ferric chloride (6 g) in water (20 ml) containing hydrochloric acid (3.7 ml conc) was added. After heating at 60°-70° C. for 20 minutes the mixture was extracted with ether. The extracts were washed with water (twice), dried over magnesium sulphate and run down under vacuum to give 4.6 g of product, which on recrystallisation from toluene gave 2.0 g pure title product, mp 124°-127° C.

Workup

  1. temperaturewere heated
  2. additionwas added
  3. temperatureAfter heating at 60°-70° C. for 20 minutes the mixture
  4. extractionwas extracted with ether
  5. washThe extracts were washed with water (twice),
  6. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-b7d7eb1dab564cbda6634660d1646766
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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