Toluene → 2-(4-Bromo-2-fluorophenyl)pyrimidine

HRID 1038104Notes

Reaction equation

HRID 1038104 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[C:4]([F:11])[CH:3]=1.Br[C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]2[N:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[C:4]([F:11])[CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 27733334-Bromo-2-fluorobenzeneboronic acid

Product 1

HCID 576857022-(4-Bromo-2-fluorophenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromo-2-fluorophenyl boronic acid (2AB) (3.0 g, 13.71 mmol, 1 equiv), 2-bromopyrimidine (1AB) (6.54 g, 41.13 mmol, 3 equiv), and 2M sodium carbonate (34 mL) were added in a pressure vessel (350 mL) and a (1v:1v) mixture of toluene and ethanol (45 mL: 45 mL) was added. The mixture was then bubbled with nitrogen gas for about 10 minutes. Tetrakistriphenylphosphine palladium (0) (793 mg, 0.686 mmol, 0.05 equiv) was added to the mixture. The reaction vessel was tightly capped, placed in an oil bath at 90° C. and stirred overnight.

Workup

  1. additionwas added
  2. customThe mixture was then bubbled with nitrogen gas for about 10 minutes
  3. customThe reaction vessel was tightly capped
  4. customplaced in an oil bath at 90° C.

Sources & evidence

ORD record
ord-6c43dc03f62748e6911c519a5e2b221e
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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