2-Chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)-4-fluoro-benzoic acid ethyl ester → 2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoic acid

HRID 1835049Notes

Reaction equation

HRID 1835049 reaction equation
C([O:3][C:4](=[O:26])[C:5]1[CH:10]=[C:9]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])[C:8]([F:24])=[CH:7][C:6]=1[Cl:25])C>C(Cl)Cl>[Cl:25][C:6]1[CH:7]=[C:8]([F:24])[C:9]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:19])([F:21])[F:20])[N:13]([CH3:22])[C:12]2=[O:23])=[CH:10][C:5]=1[C:4]([OH:26])=[O:3]

Participants

3

Reactant 1

HCID 129938562-Chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)-4-fluoro-benzoic acid ethyl ester

Product 1

HCID 120567892-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-(3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl)-4-fluoro-benzoic acid ethyl ester (5.2 g) was dissolved in methylenechloride (100 ml) and borontribromide (10 g) was added dropwise at ambient temperature. The reaction mixture was stirred for three hours at this temperature and poured into ice-water. The resulting mixture was extracted with ethyl acetate. The organic phase was washed with brine (×3) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to give the titled compound (4.3 g) as a white solid.

Workup

  1. additionborontribromide (10 g) was added dropwise at ambient temperature
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with brine (×3)
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-19ff8dab61094e3db7932c99dd544ff0
Source dataset
uspto-grants-2004_08
Patent number
US06770597B2

Reaction notes

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