Bromine → HCID 20130602, compound

HRID 1252928Notes

Reaction equation

HRID 1252928 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:15]=[C:14]([F:16])[C:13]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([CH3:24])[NH:19][C:18]2=[O:25])=[CH:12][C:5]=1[C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7]>C(O)(=O)C>[Cl:3][C:4]1[CH:15]=[C:14]([F:16])[C:13]([N:17]2[C:22](=[O:23])[C:21]([Br:1])=[C:20]([CH3:24])[NH:19][C:18]2=[O:25])=[CH:12][C:5]=1[C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7]

Participants

4

Reactant 2

HCID 24408BromineHCID 19994231HCID 19994231, compound

Product 1

HCID 20130602HCID 20130602, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 1.7 g of bromine in 20 ml of acetic acid is added dropwise with stirring to a solution of 3.4 g of isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate in 20 ml of acetic acid at 25° C. during 25 minutes. The reaction mixture is stirred for a further hour and evaporated to dryness under reduced pressure. The residue is dissolved in diethyl ether and washed with aqueous sodium bicarbonate solution, thereafter with water. The organic phase is dried over anhydrous sodium sulphate and evaporated to dryness. The residue is recrystallized from diethyl ether/n-hexane. There is obtained isopropyl 2-chloro-4-fluoro-5-[5-bromo-3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, m.p. 187°-189° C.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe residue is dissolved in diethyl ether
  3. washwashed with aqueous sodium bicarbonate solution
  4. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  5. customevaporated to dryness
  6. customThe residue is recrystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-39350cd842e849fc8e20945536e170ef
Source dataset
uspto-grants-1988_05
Patent number
US04746352

Reaction notes

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