Bromobenzene → 1-Benzyl-alpha-phenyl-alpha-(p-trifluoromethylphenyl)-imidazole-2-methanol

HRID 261966

반응식

HRID 261966 반응식
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([Li])C=CC=CC=1.[Li].BrC1C=CC=CC=1.[F:28][C:29]([F:45])([F:44])[C:30]1[CH:43]=[CH:42][C:33]([C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:35])=[CH:32][CH:31]=1>O.O1CCCC1.C(OCC)C>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:33]1[CH:32]=[CH:31][C:30]([C:29]([F:45])([F:44])[F:28])=[CH:43][CH:42]=1)[OH:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

9

반응물 5

HCID 7961BromobenzeneHCID 697674-(Trifluoromethyl)benzophenoneHCID 779181-BenzylimidazoleHCID 3028194LithiumHCID 178506676HCID 178506676, 화합물

생성물 1

HCID 124339341-Benzyl-alpha-phenyl-alpha-(p-trifluoromethylphenyl)-imidazole-2-methanol

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 14.2 g (0.09 mol) of 1-benzylimidazole (A. M. Roe, J. Chem. Soc., 1963, 2195) in 60 ml. of tetrahydrofuran was added dropwise at -20° to -30° C. under a nitrogen atmosphere to 0.1 mol phenyl lithium (prepared from 1.52 g (0.22 gr. at.) of lithium and 15.7 g (0.19 mol) of bromobenzene) in 70 ml. of diethyl ether. The reaction mixture was stirred for one hour and then 22.5 g (0.09 mol) of 4-(trifluoromethyl)benzophenone in 35 ml. of tetrahydrofuran were added dropwise. The reaction mixture was stirred under the nitrogen atmosphere for two hours at -20° to -30° C. and for 15 hours at room temperature. The mixture was then poured into a mixture of ice and water. The aqueous phase was twice extracted with diethyl ether and the combined extracts were concentrated. The residue was taken up in diethyl ether and the undissolved solid matter (ketone starting material) was filtered off. The ether was distilled off and the residue was again taken up in a small amount of diethyl ether. The undissolved material, which now appeared to be the desired product, was filtered off. This procedure (evaporating the ether and taking up the residue in ether again) was repeated a few times and the solid materials filtered off were combined. The substance was crystallised from isopropyl alcohol with a small amount of water. 1-Benzyl-α-phenyl-α-(p-trifluoromethylphenyl)-imidazole-2-methanol was obtained.

후처리

  1. stirringThe reaction mixture was stirred under the nitrogen atmosphere for two hours at -20° to -30° C. and for 15 hours at room temperature
  2. extractionThe aqueous phase was twice extracted with diethyl ether
  3. concentrationthe combined extracts were concentrated
  4. filtrationthe undissolved solid matter (ketone starting material) was filtered off
  5. distillationThe ether was distilled off
  6. filtrationwas filtered off
  7. customThis procedure (evaporating the ether
  8. filtrationthe solid materials filtered off
  9. customThe substance was crystallised from isopropyl alcohol with a small amount of water

출처 및 근거

ORD 기록
ord-e8fb85978faf4c0dbdc0db946d7a5e24
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04152441

연결된 노트

불러오는 중…