Carbon tetrabromide → 3-(4-bromomethylphenyl)-1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazole

HRID 1038308

反応式

HRID 1038308 の反応式
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:45]>C1COCC1>[Br:45][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:13]=[CH:14][N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:24])([F:23])[F:1])=[CH:5][CH:6]=3)[N:11]=2)=[CH:16][CH:17]=1

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66776992{4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-phenyl}-methanol

生成物 1

HCID 667770563-(4-bromomethylphenyl)-1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazole収率 77.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of {4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-phenyl}-methanol (P-6; 5.033 g, 15.01 mmol) in THF (100 mL) was added triphenylphosphine (6.009 g, 22.91 mmol). Carbon tetrabromide (7.704 g, 23.23 mmol) dissolved in THF (20 mL) was then added dropwise at room temperature. The mixture was allowed to stir at room temperature for 23 h. It was then filtered through Celite, and the solvent was evaporated at room temperature under vacuum. The crude material was purified by silica gel chromatography, eluting with 50% EtOAc/hexane going to 70% EtOAc/hexane and then 100% EtOAc in a two-step gradient. The title product (4.61 g, 77%) was isolated as a beige solid: mp 124-126° C.; 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.25-8.13 (m, 2H), 7.89-7.72 (m, 2H), 7.60-7.47 (m, 2H), 7.47-7.34 (m, 2H), 4.57 (s, 2H); ESIMS m/z 400 (M+2H), 399 (M+H).

後処理

  1. additionwas then added dropwise at room temperature
  2. filtrationIt was then filtered through Celite
  3. customthe solvent was evaporated at room temperature under vacuum
  4. customThe crude material was purified by silica gel chromatography
  5. washeluting with 50% EtOAc/hexane going to 70% EtOAc/hexane

出典と根拠

ORDレコード
ord-a3bc15047ab049ecbf9d63990fa29676
出典データセット
uspto-grants-2013_10
特許番号
US08551914B2

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