Triacetoxyperiodinane → (2-Bromo-3-methylphenyl)(pyrimidin-4-yl)methanone

HRID 1028978Notes

Reaction equation

HRID 1028978 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][N:12]=1)[OH:10].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O.O.O.O.O.S1(OSO1)(=O)=O.[Na]>C(Cl)Cl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][N:12]=1)=[O:10]

Participants

6

Reactant 4

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2×HCID 67324212(2-Bromo-3-methylphenyl)(pyrimidin-4-yl)methanolHCID 86676839Sodium thio sulfate pentahydrate

Product 1

HCID 67324109(2-Bromo-3-methylphenyl)(pyrimidin-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-bromo-3-methylphenyl)(pyrimidin-4-yl)methanol (0.40 g, 1.433 mmol) in DCM (10 mL) were added sodium bicarbonate (0.223 mL, 5.73 mmol) and Dess-Martin periodinane (0.790 g, 1.863 mmol) in one portion. The resulting mixture was stirred at RT for 1 h then quenched with sat NaHCO3 and sodium thio sulfate pentahydrate (1.778 g, 7.17 mmol). The quenched mixture was stirred for 1 h more and extracted with DCM. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to afford (2-bromo-3-methylphenyl) (pyrimidin-4-yl)methanone which was used without purification.

Workup

  1. stirringThe quenched mixture was stirred for 1 h more
  2. extractionextracted with DCM
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bb258ee4414f4c29b27000ba523a5e40
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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