Chlorohydroxy benzophenone → HCID 69275104, compound

HRID 2219214Notes

Reaction equation

HRID 2219214 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:16])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])[CH:7]=1.[Br:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:17][CH2:18][CH2:19][O:16][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9]

Participants

5

Reactant 3

HCID 6799Chlorohydroxy benzophenoneHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 69275104HCID 69275104, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (5-chloro-2-hydroxy-phenyl)-phenyl-methanone (0.93 g, 4.0 mmol), δ 1,2-dibromoethane (3.5 mL, 40 mmol) and potassium carbonate (0.83 g, 6.0 mmol) in acetonitrile (10 mL) is heated at reflux under N2 over weekend (about 60 hours). After cooling to room temperature, solid potassium bromide is filtered off and washed with ca. 70 mL of acetonitrile. The filtrate is evaporated, and the crude mixture purified by column chromatography (SiO2, 5-12% ethyl acetate in hexanes) to afford 1.18 g (87%) of the title compound as colorless product. APCI-MS: m/z 339 [(M+H)+, 35Cl, 79Br], 341 [(M+H)+, 37Cl, 79Br], 343 [(M+H)+, 37Cl, 81Br]. 1H-NMR (300 MHz; CDCl3): δ7.78 (2H d, 8.1 Hz); 7.58 (1H, br t, 7.5 Hz); 7.38-7.50 (4H, m); 6.92 (1H, d, 8.6 Hz); 4.18 (2H, t; 6.5 Hz); 3.26 (2H, t, 6.5 Hz).

Workup

  1. temperatureis heated
  2. temperatureat reflux under N2 over weekend (about 60 hours)
  3. filtrationsolid potassium bromide is filtered off
  4. washwashed with ca. 70 mL of acetonitrile
  5. customThe filtrate is evaporated
  6. customthe crude mixture purified by column chromatography (SiO2, 5-12% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1b43be936967489dacafced2d536bfca
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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