Water → HCID 13163448, compound

HRID 1776799Notes

Reaction equation

HRID 1776799 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.[C:12]1([NH:18]N)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C(O)C.C(O)(=O)C.C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8]2[NH:18][C:12]3[C:17]([CH:9]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:7]=1

Participants

7

Reactant 3

HCID 962Water2×HCID 7516PhenylhydrazineHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 13163448HCID 13163448, compoundYield 22.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 702EthanolSolventHCID 7237O-XyleneSolvent

Procedure

1-(5-bromo-2-hydroxyphenyl)ethanone (7.1 g, 33 mmol) and phenylhydrazine (4.3 g, 40 mmol) were stirred in 45 mL of dry ethanol. Acetic acid (27 drops) was added and the mixture was refluxed for 5 hours. After cooling to room temperature, the precipitates were collected by filtration to provide the crude product as a light yellow solid, which was stirred in 100 mL of xylene and 50 g of polyphosphoric acid at 85° C. for 8 hours. Water was added to the warm crude, and then the mixture was stirred for 10 minutes before poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (petroleum ether:EtOAc=10:1) provided 4-bromo-2-(1H-indol-2-yl)phenol as a light yellow powder (2.1 g, 22.1%). 1H-NMR (CDCl3, 400 MHz) δ 10.08 (s, 1H), 9.56 (s, 1H), 7.88 (s, 1H), 7.61 (d, J=8.0 Hz, 1H), 7.38 (d, J=8.0 Hz, 1H), 7.14˜7.19 (m, 2H), 7.08 (t, J=7.2 Hz, 1H), 6.8˜56.88 (m, 2H). MS (M+H)+: 288/290.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. filtrationthe precipitates were collected by filtration
  3. customto provide the crude product as a light yellow solid, which
  4. temperaturewarm crude
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by flash chromatography on silica gel (petroleum ether:EtOAc=10:1)

Sources & evidence

ORD record
ord-a4c5ef70b0a949b0a493e5b0e790d8a0
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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