Uracil → 5-Bromouracil

HRID 1742758Notes

Reaction equation

HRID 1742758 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[Br:9]Br>C(O)(=O)C>[Br:9][C:7]1[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][CH:8]=1

Participants

4

Reactant 2

HCID 1174UracilHCID 24408Bromine

Product 1

HCID 58025-BromouracilYield 90.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

39.4 g (0.35 mol) of uracil are dissolved in 200 ml of acetic acid, and the mixture is warmed to 70° C. The mixture is added dropwise over the course of 2 hours to a solution of 20 ml (0.38 mol) of bromine dissolved in 200 ml of acetic acid. The orange suspension is held at 70° C. overnight and then cooled to 0°-5° C. The precipitate obtained is filtered off, washed with 200 ml of cold water and dried, giving 60.2 g of 5-bromouracil (89.7% of theory).

Workup

  1. temperaturecooled to 0°-5° C
  2. customThe precipitate obtained
  3. filtrationis filtered off
  4. washwashed with 200 ml of cold water
  5. customdried

Sources & evidence

ORD record
ord-0bf659bb78b8479aae40234d5a87bc1a
Source dataset
uspto-grants-1994_08
Patent number
US05340701

Reaction notes

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