Carbon Dioxide → 3-Bromo-2,5,6-trifluorobenzoic acid

HRID 577285

반응식

HRID 577285 반응식
C([Li])CCC.C(NC(C)C)(C)C.[Li+].CC([N-]C(C)C)C.[F:21][C:22]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:23]=1[Br:30].[C:31](=[O:33])=[O:32].Cl>C1COCC1.C(OCC)C>[Br:30][C:23]1[C:22]([F:21])=[C:27]([C:26]([F:28])=[C:25]([F:29])[CH:24]=1)[C:31]([OH:33])=[O:32]

참가 물질

9

반응물 6

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 675971-Bromo-2,4,5-trifluorobenzeneHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

생성물 1

HCID 142788253-Bromo-2,5,6-trifluorobenzoic acid수율 52.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

n-Butyllithium (2.5M in hexane, 10.5 mL, 1.1 eq.) was added dropwise over 15 min to a solution of diisopropylamine (4.0 mL, 1.2 eq.) in THF (25 mL) at 0° C. After stirring for 15 min, the LDA solution was added dropwise over 40 min to a solution of 2,4,5-trifluorobromobenzene (5.0 g, 24 mmol) in THF (50 mL) at −78° C. The solution was stirred for 10 min and then transferred to a slurry of dry ice (50 g) in diethylether (65 mL). The reaction was allowed to warm to rt and treated with 1M HCl. The phases were separated and the organic layer extracted with 0.5M NaOH. The basic extracts were acidified to pH 1 with 6M HCl and extracted with diethylether. The combined organic phases were dried over sodium sulfate and evaporated to yield 3-bromo-2,5,6-trifluorobenzoic acid as a white solid (3.2 g, 52%).

후처리

  1. stirringThe solution was stirred for 10 min
  2. customThe phases were separated
  3. extractionthe organic layer extracted with 0.5M NaOH
  4. extractionextracted with diethylether
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated

출처 및 근거

ORD 기록
ord-8b1b2365dc3c4641836a9106b2ab1788
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040545B2

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