Iodine → 6-Chloro-2-fluoroquinoline

HRID 342883

반응식

HRID 342883 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.II.C(N(CC)CC)C.[F:21]F>S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>[F:21][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=1

참가 물질

6

반응물 4

HCID 807IodineHCID 8471TriethylamineHCID 24524Fluorine2회HCID 691636-Chloroquinoline

생성물 1

HCID 6394426-Chloro-2-fluoroquinoline수율 93%

시약·촉매·용매 1

HCID 656671Sodium Pyrosulfite용매

실험 절차

A solution containing 6-chloroquinoline (1.0 g, 6.1 mmol), iodine (1.55 g, 6.1 mmol) and triethylamine (0.62 g, 6.2 mmol) in CF2ClCFCl2 (30 ml) was placed in a fluorination apparatus fitted with a drying tube filled with soda lime. Elemental fluorine (7 mmol) as a 10% mixture in dry nitrogen was then passed through the stirred solution using narrow bore PTFE tubing at ca. 15 ml/min. After the fluorine had been added the solution was poured into 10% aqueous sodium metabisulfite solution (30 ml) and extracted with dichloromethane. The organic extracts were dried and evaporated to a brown solid (1.03 g). GC/MS analysis showed a 79% conversion of starting material. Column chromatography on silica gel with dichloromethane as eluant gave 2-fluoro-6-chloroquinoline (0.82 g, 93%), RF 0.78 (CH2Cl2); δH (400 MHz CDCl3, Me4Si) 7.12 ppm (1H, d d, JH3,H4 8.8, JH3,F 2.8, H-3), 7.67 (1H, d d, JH7,H8 9.2, JH5,H7 2.4, H-7), 7.82 (1H, d, JH5,H7 2.4, H-5), 7.87 (1H, d, JH7,H8 9.0, H-8), 8.16 (1H, d d, JH3,H4 =JH4,F 8.8, H-4);δC (100 MHz, CDCl3, Me4Si) 111.1 ppm (d, 2J 42.3, C-3), 126.3 (s, C-5), 127.3 (s, C-4a), 129.6 (s, C-8), 131.4 (s, C-7), 131.9 (s, C-6) 141.0 (d,3J 9.9, C-4), 144.1 (d 3J 16.8, C-8a), 161.2 (d, 1J 243.8, C-2); δF (235 MHz, CDC13, CFCl3) -61.5 ppm (s); m/z (E1+) 181 (M+, 100%), 183 (M+, 32), 146 (34), 126 (11).

후처리

  1. customfitted with a drying tube
  2. extractionextracted with dichloromethane
  3. customThe organic extracts were dried
  4. customevaporated to a brown solid (1.03 g)

출처 및 근거

ORD 기록
ord-cc41aa8bb74d4642a63c643b45281b86
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859255

연결된 노트

불러오는 중…