Water → alpha,alpha-Bis(4-bromophenyl)-5-pyrimidinemethanol

HRID 1492913Notes

Reaction equation

HRID 1492913 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1.[Br:13][C:14]1[CH:28]=[CH:27][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)=[O:19])=[CH:16][CH:15]=1.O>CCCCCC.C1COCC1>[Br:13][C:14]1[CH:28]=[CH:27][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)([C:7]2[CH:8]=[N:9][CH:10]=[N:11][CH:12]=2)[OH:19])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 728684,4'-DibromobenzophenoneHCID 783445-BromopyrimidineHCID 178418339Butyllithium

Product 1

HCID 19043035alpha,alpha-Bis(4-bromophenyl)-5-pyrimidinemethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 20 ml of 1.6N n-butyllithium in hexane is added dropwise within 30 minutes, with stirring and with the exclusion of moisture, to a solution, cooled to -75°, of 5.2 g (33 mmol) of 5-bromopyrimidine and 10.7 g (31.2 mmol) of 4,4'-dibromobenzophenone in 130 ml of THF. The reaction mixture is stirred for a further 0.5 hour at -75° and then for 16 hours at room temperature; then, while cooling with ice, it is hydrolysed by adding 20 ml of water. The organic phase is separated and diluted with ethyl acetate. The solution is washed with 2N HCl and a semi-saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated by evaporation. The residue is purified by column chromatography (400 g of silica gel, methylene chloride/ethyl acetate 85:15) and recrystallised from ethyl acetate, m.p. 89°-90°, Rf value=0.11 (silica gel, methylene chloride/ethyl acetate 85:15).

Workup

  1. stirringThe reaction mixture is stirred for a further 0.5 hour at -75°
  2. temperaturethen, while cooling with ice, it
  3. customThe organic phase is separated
  4. additiondiluted with ethyl acetate
  5. washThe solution is washed with 2N HCl
  6. dry with materiala semi-saturated sodium chloride solution, dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customThe residue is purified by column chromatography (400 g of silica gel, methylene chloride/ethyl acetate 85:15)
  10. customrecrystallised from ethyl acetate, m.p. 89°-90°, Rf value=0.11 (silica gel, methylene chloride/ethyl acetate 85:15)

Sources & evidence

ORD record
ord-6651a414f95c49eb9db81b992f1b13f8
Source dataset
uspto-grants-1994_12
Patent number
US05376669

Reaction notes

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