Carbon Dioxide → 2,6-Difluoro-4-pentylbenzoic acid

HRID 466494노트

반응식

HRID 466494 반응식
C([Li])CCC.[F:6][C:7]1[CH:8]=[C:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:10]=[C:11]([F:13])[CH:12]=1.[C:19](=[O:21])=[O:20].CCOCC>C1COCC1>[F:6][C:7]1[CH:8]=[C:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:10]=[C:11]([F:13])[C:12]=1[C:19]([OH:21])=[O:20]

참가 물질

6

반응물 4

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 157519781,3-Difluoro-5-pentylbenzeneHCID 178418339Butyllithium

생성물 1

HCID 190101792,6-Difluoro-4-pentylbenzoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of n-butyllithium (10.5M in hexane; 2.70 ml, 0.028 mol) was added dropwise to a stirred, cooled (-78° C.) solution of compound 13 (5.10 g, 0.028 mol) in dry THF (30 ml) under dry nitrogen. The stirred mixture was maintained under these conditions for 2.5 h and then poured onto a slurry of solid carbon dioxide and dry ether. The product was extracted into 10% sodium hydroxide which was then acidified with 36% hydrochloric acid. The acidic mixture was washed with ether (twice), and the combined ethereal layers were washed with water and dried (MgSO4). The solvent was removed in vacuo to yield a colourless solid.

후처리

  1. temperatureThe stirred mixture was maintained under these conditions for 2.5 h
  2. extractionThe product was extracted into 10% sodium hydroxide which
  3. washThe acidic mixture was washed with ether (twice), and the combined ethereal layers
  4. washwere washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customto yield a colourless solid

출처 및 근거

ORD 기록
ord-eecfd88f3d4945319632e1940c5c7162
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05156763

반응 노트

불러오는 중…