Methanol → 4-(5-Bromopyrimidin-2-yl)-3,5-difluorophenol

HRID 42007Notes

Reaction equation

HRID 42007 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[C:13]([F:14])=[CH:12][C:11]([O:15]C)=[CH:10][C:9]=2[F:17])=[N:6][CH:7]=1.B(Br)(Br)Br.CO.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[C:9]([F:17])=[CH:10][C:11]([OH:15])=[CH:12][C:13]=2[F:14])=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 673942495-Bromo-2-(2,6-difluoro-4-methoxyphenyl)pyrimidine

Product 1

HCID 1361955854-(5-Bromopyrimidin-2-yl)-3,5-difluorophenolYield 96.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-2-(2,6-difluoro-4-methoxyphenyl)pyrimidine (0.887 g, 2.95 mmol) in DCM at 0° C., was added dropwise a solution of BBr3 (1M in DCM) (22 ml, 22 mmol) and the reaction mixture was stirred overnight at room temperature. This mixture was then poured over cold MeOH and solid NaHCO3 was added slowly until pH=4-5. The suspension obtained was filtered and the filtrate evaporated. The solid obtained was redissolved in ethyl acetate, washed with water and brine, dried and concentrated to give the desired compound as a white solid (0.817 g, 85% of yield).

Workup

  1. additionwas added slowly until pH=4-5
  2. customThe suspension obtained
  3. filtrationwas filtered
  4. customthe filtrate evaporated
  5. customThe solid obtained
  6. washwashed with water and brine
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-18d6551235cd4ddda8d73eb9a4e6944b
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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