2-Bromo-1-(4-hydroxyphenyl)ethanone → HCID 18419586, compound

HRID 1374929Notes

Reaction equation

HRID 1374929 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:4].[CH3:12][C:13]1[N:14]=[CH:15][S:16][C:17]=1[CH3:18].COC(C)(C)C>C(#N)C>[Br-:1].[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N+:14]2[C:13]([CH3:12])=[C:17]([CH3:18])[S:16][CH:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 15413tert-Butyl methyl etherHCID 625104,5-Dimethylthiazole

Product 1

HCID 18419586HCID 18419586, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

The neat mixture of 2-bromo-4′-hydroxyacetophenone (3 g, 15 mmol) and 4,5-dimethylthiazole (1.71 g, 15 mmol) was heated at 110° C. for 3 hrs. It was dissolved in acetonitrile (15 mL) and cooled to room temperature. Tert-butyl methyl ether (5 mL) was added and the reaction mixture kept at room temperature overnight. The product crystallized was filtered, washed well with a mixture of acetonitrile and tert-butyl methyl ether (1:1, v/v) and dried. It was recrystallized from a mixture of acetonitrile, ethyl alcohol and tert-butyl methyl ether. Yield: 3.18 g (64%); mp. 245–247° C. (dec.).

Workup

  1. temperaturecooled to room temperature
  2. customThe product crystallized
  3. filtrationwas filtered
  4. washwashed well with a mixture of acetonitrile and tert-butyl methyl ether (1:1
  5. customv/v) and dried
  6. customIt was recrystallized from a mixture of acetonitrile, ethyl alcohol and tert-butyl methyl ether

Sources & evidence

ORD record
ord-5aa0eaee7ef7457698deb5e9cb9aa085
Source dataset
uspto-grants-2007_01
Patent number
US07166625B2

Reaction notes

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