Water → 4-[(2,3-Dihydro-1H-inden-2-yl)sulfanyl]phenol

HRID 1388585Notes

Reaction equation

HRID 1388585 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH:10]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 25134Boron tribromideHCID 576069HCID 576069, compound

Product 1

HCID 204713974-[(2,3-Dihydro-1H-inden-2-yl)sulfanyl]phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(p-methoxyphenylthio) indane (5 g) in dry dichloromethane (40 ml) was cooled to -70°. Boron tribromide (6 g) was added slowly with stirring at -70°. When addition was complete, the reaction mixture was kept at -70° for a further 10 minutes and then allowed to warm to room temperature. The mixture was left overnight and water (70 ml) then added slowly with stirring. The mixture was then poured into water (65 ml) and a further quantity (95 ml) of dichloromethane added, and the mixture agitated. The dichloromethane solution was separated and extracted with 2 molar sodium hydroxide. The cloudy extract was allowed to stand until it cleared and was then decanted from a residue. The solution was acidified with dilute hydrochloric acid and extracted with ether. The ether solution was washed with water, dried, and evaporated to give 2-(p-hydroxyphenylthio)indane.

Workup

  1. additionWhen addition
  2. waitThe mixture was left overnight
  3. stirringwith stirring
  4. stirringthe mixture agitated
  5. customThe dichloromethane solution was separated
  6. extractionextracted with 2 molar sodium hydroxide
  7. extractionThe cloudy extract
  8. customwas then decanted from a residue
  9. extractionextracted with ether
  10. washThe ether solution was washed with water
  11. customdried
  12. customevaporated

Sources & evidence

ORD record
ord-c38ad78c21cc46d5af7ab437854db6eb
Source dataset
uspto-grants-1984_02
Patent number
US04431834

Reaction notes

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