Water → 3'-(Hydroxymethyl)-5'-(trifluoromethyl)biphenyl-4-carbonitrile

HRID 391370

反応式

HRID 391370 の反応式
Br[C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)#[N:15].[OH-].[K+].O>C1COCC1.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:13][CH2:12][C:4]1[CH:3]=[C:2]([C:19]2[CH:20]=[CH:21][C:16]([C:14]#[N:15])=[CH:17][CH:18]=2)[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1

参加物

8

反応物 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 27343264-Cyanophenylboronic acidHCID 29919767[3-Bromo-5-(trifluoromethyl)phenyl]methanol

生成物 1

HCID 589936723'-(Hydroxymethyl)-5'-(trifluoromethyl)biphenyl-4-carbonitrile収率 51%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

A solution of (3-bromo-5-(trifluoromethyl)phenyl)methanol (3.0 g, 11.8 mmol), 4-cyanophenyl boronic acid (5.2 g, 35 mmol), tetrakis(triphenylphosphine) palladium(0) (2.7 g, 2.4 mmol), and aqueous potassium hydroxide (41 mL, 1N, 41 mmol) in THF (80 mL) was degassed with nitrogen for 10 minutes and then heated at 120° C. for 18 hours. The reaction was cooled to ambient temperature and poured into water (100 mL), then was diluted with ethyl acetate (100 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (2×20 mL) and the combined organic layers were dried with MgSO4 and evaporated. The residue was purified by chromatography on SiO2 with a gradient of ethyl acetate/hexanes of 5%-40%. The product 3′-(hydroxymethyl)-5′-(trifluoromethyl)biphenyl-4-carbonitrile (1.66 g, 51%) was obtained as a white solid. 1H-NMR (CDCl3, 400 MHz) δ 7.65-7.80 (m, 7H), 4.85 (s, 2H), 1.90 (bs, 1H). Mass spec.: 278.2 (M+H).

後処理

  1. temperatureThe reaction was cooled to ambient temperature
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  4. dry with materialthe combined organic layers were dried with MgSO4
  5. customevaporated
  6. customThe residue was purified by chromatography on SiO2 with a gradient of ethyl acetate/hexanes of 5%-40%

出典と根拠

ORDレコード
ord-2bdd23daea614f9c8d1f158af53d56d0
出典データセット
uspto-grants-2013_02
特許番号
US08383821B2

関連ノート

読み込み中…