Boron tribromide → 2,4,6-Trichloropyrimidin-5-ol

HRID 528435Notes

Reaction equation

HRID 528435 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([O:9]C)=[C:4]([Cl:11])[N:3]=1.B(Br)(Br)Br>C(Cl)Cl.CO.O>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 2

HCID 25134Boron tribromideHCID 202711362,4,6-Trichloro-5-methoxypyrimidine

Product 1

HCID 866673322,4,6-Trichloropyrimidin-5-olYield 71%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of nitrogen a solution of 2,4,6-trichloro-5-methoxy-pyrimidine (4.0 g, 18.7 mmol) in DCM (200 mL) was cooled to 0° C. and treated with boron tribromide (6.6 mL, 65 mmol) dropwise. After stirring for 18 hours at RT the reaction mixture was cooled and diluted with methanol (25 mL, CARE, EXOTHERM!) and the reaction mixture diluted with water (200 mL). The aqueous layer was extracted with DCM and the combined organic extracts dried (Na2SO4) and concentrated in vacuo to give 2,4,6-Trichloro-5-hydroxy-pyrimidine as a pale tan solid (2.55 g, 71%). 13C NMR (DMSO-d6): 149.23 (C), 145.25 (C), 145.08 (C). LCMS (Method C): RT=2.65/2.77. [M−H]+ 197/199.

Workup

  1. temperaturewas cooled
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialthe combined organic extracts dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5dc69e7a60a4ccd8f8a15ccb2fe835c
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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