Carbon Dioxide → 3,5-Dibromo-2-fluorobenzoic acid

HRID 1612449노트

반응식

HRID 1612449 반응식
C([Li])CCC.CC1(C)CCCC(C)(C)N1.[Br:16][C:17]1[CH:22]=[C:21]([Br:23])[CH:20]=[CH:19][C:18]=1[F:24].[C:25](=[O:27])=[O:26]>C1COCC1.O.[OH-].[Na+]>[Br:16][C:17]1[C:18]([F:24])=[C:19]([CH:20]=[C:21]([Br:23])[CH:22]=1)[C:25]([OH:27])=[O:26]

참가 물질

8

반응물 4

HCID 280Carbon DioxideHCID 130352,2,6,6-TetramethylpiperidineHCID 150342,4-Dibromo-1-fluorobenzeneHCID 178418339Butyllithium

생성물 1

HCID 27739703,5-Dibromo-2-fluorobenzoic acid

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

실험 절차

Butyllithium (1.6M solution in hexanes, 12.3 ml, 19.7 mmol) was added dropwise to a solution of 2,2,6,6-tetramethylpiperidine (3.32 ml, 19.7 mmol) in THF at −78° C. The reaction was stirred for 10 min. prior to the addition of 2,4-dibromofluorobenzene (5 g, 19.7 mmol). Stirring was continued for 2 h. The solution was then poured onto freshly crushed dry ice and allowed to warm to room temperature. The resulting solution was diluted with water (100 ml) and NaOH (2M, 10 ml) was added. This was extracted with ether (2×) and the aqueous layer was acidified to pH 1 (2M HCl) to afford a gummy solid which was triturated from ether to afford the title compound (D37) as a colourless solid (1.23 g).

후처리

  1. stirringStirring
  2. waitwas continued for 2 h
  3. additionwas added
  4. extractionThis was extracted with ether (2×)
  5. customto afford a gummy solid which
  6. customwas triturated from ether

출처 및 근거

ORD 기록
ord-4008d10acd9840fb96733d4a9e4645be
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06992103B2

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