Ethanol → 2-[(4-Bromophenyl)methyl]-1H-indole

HRID 248920Notes

Reaction equation

HRID 248920 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[N:10](C(OC(C)(C)C)=O)[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:4][CH:3]=1.[OH-].[Na+].C(O)C>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 18946927HCID 18946927, compound

Product 1

HCID 107795362-[(4-Bromophenyl)methyl]-1H-indoleYield 49.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of t-butyl 2-(p-bromophenylmethyl)indole-1-carboxylate (F) (6.0 g) (prepared, e.g., as described in Preparation 2), 10% sodium hydroxide in water (20 ml), and ethanol (150 ml), was heated under reflux for 6 hours. The mixture was then poured onto a mixture of ice water/dilute brine and extracted twice with ethyl acetate. The extract was washed with brine and dried over magnesium sulphate. The solvent was evaporated under reduced pressure to produce an oil, which then crystallized. The material was recrystallized from methyl t-butyl ether to give 2-(p-bromophenylmethyl)indole (2.2 g), a compound of Formula (G), m.p. 136° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. extractionextracted twice with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customThe solvent was evaporated under reduced pressure
  7. customto produce an oil, which
  8. customthen crystallized
  9. customThe material was recrystallized from methyl t-butyl ether

Sources & evidence

ORD record
ord-c8096c0e7e9049aa9deebdbb1231d329
Source dataset
uspto-grants-1993_05
Patent number
US05212195

Reaction notes

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