Hydrochloric Acid → 2-Hydroxydibenzothiophene

HRID 1606769Notes

Reaction equation

HRID 1606769 reaction equation
C([Li])CCC.Br[C:7]1[CH:19]=[CH:18][C:10]2[S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:9]=2[CH:8]=1.B(OCCCC)(OCCCC)[O:21]CCCC.OO.Cl>CCOCC>[OH:21][C:7]1[CH:19]=[CH:18][C:10]2[S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:9]=2[CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 12712Tributyl borateHCID 2995082-BromodibenzothiopheneHCID 178418339Butyllithium

Product 1

HCID 1556252-HydroxydibenzothiopheneYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Butyl lithium (0.05 mole) in ether was added to 2-bromodibenzothiophene (13.15 g, 0.05 mole) in 150 ml dry ether at 0°C. The mixture was then cooled to -70° and freshly distilled tributyl borate (11.5 g, 0.05 mole) dissolved in 50 ml ether was added. The reaction mixture was stirred for 2 hours, and was then allowed to warm up to room temperature. Perhydrol (10 ml) was added and the mixture was refluxed for 1.5 hours. Hydrochloric acid was added and the organic phase was separated. The ether was washed with 10 % ferrous ammonium sulphate solution and then extracted with sodium hydroxide solution. The alkaline aqueous solution was acidified and extracted with ether, which after evaporation gave 8.6 g (86 %) of the desired product. Recrystallization from ligroin gave white crystals with m.p. 152°-155°.

Workup

  1. temperatureThe mixture was then cooled to -70°
  2. additionwas added
  3. temperaturethe mixture was refluxed for 1.5 hours
  4. customthe organic phase was separated
  5. washThe ether was washed with 10 % ferrous ammonium sulphate solution
  6. extractionextracted with sodium hydroxide solution
  7. extractionextracted with ether, which
  8. customafter evaporation

Sources & evidence

ORD record
ord-5793275e95a14813afc7406cbba0abda
Source dataset
uspto-grants-1976_04
Patent number
US03953601

Reaction notes

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