Boron tribromide → HCID 67405891, compound

HRID 869291Notes

Reaction equation

HRID 869291 reaction equation
[Cl:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([O:10]C)=[CH:4][N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([OH:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66519725HCID 66519725, compound

Product 1

HCID 67405891HCID 67405891, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1.18 g (6.76 mmol) 2-chloro-5-methoxy-3-methylpyrimidin-4(3H)-one in 35 ml CH2Cl2 was added 47.3 ml (47.3 mmol) of a 1 M solution of BBr3 in CH2Cl2. The reaction mixture was stirred for 1 h, cooled to 0° C., quenched with 100 ml MeOH, and concentrated in vacuo. The solid was suspended in ether, and collected by filtration to give 1.09 g (100% yield) of 2-chloro-5-hydroxy-3-methylpyrimidin-4(3H)-one. LCMS [M+H]+=161.0.

Workup

  1. customquenched with 100 ml MeOH
  2. concentrationconcentrated in vacuo
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-996cff106c4c49d4a96fa663622a5b27
Source dataset
uspto-grants-2015_03
Patent number
US08969364B2

Reaction notes

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