2-Bromophenol → HCID 21865142, compound

HRID 857692Notes

Reaction equation

HRID 857692 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[H-].[Na+].Cl[C:12]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:15]=[CH:14][N:13]=1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:12]1[CH:17]=[C:16]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:23]=2)[N:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 24758Sodium hydrideHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine

Product 1

HCID 21865142HCID 21865142, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromophenol (2.595 g, 15 mmol, Aldrich) in anhydrous DMF (20 mL) was added NaH (0.68 g, 17 mmol, 60% suspension in mineral oil, Aldrich) in small portions with stirring at room temperature. The reaction mixture was stirred for 0.5 h at room temperature and 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (2.586 g, 10 mmol) was added in one portion. The reaction mixture was stirred for 18 h at room temperature and most of the solvent was removed in vacuo. The residue was dissolved in EtOAc, washed with 1N NaOH (2×) and H2O, dried over Na2SO4, filtered and concentrated in vacuum. The residue was recrystallized from EtOAc/hexane to give 3.21 g (81%) of the title compound. MS (ESI, pos. ion) m/z: 397 (M+1).

Workup

  1. stirringThe reaction mixture was stirred for 0.5 h at room temperature
  2. stirringThe reaction mixture was stirred for 18 h at room temperature and most of the solvent
  3. customwas removed in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with 1N NaOH (2×) and H2O
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. customThe residue was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-d7301dc0b7b24273af917cd9da02abc7
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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