(4'-Bromo-4-(dimethylamino)biphenyl-2-yl)methanol → 4'-Bromo-4-(dimethylamino)biphenyl-2-carbaldehyde

HRID 1043437ノート

反応式

HRID 1043437 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]([CH3:16])[CH3:15])=[CH:10][C:9]=2[CH2:17][OH:18])=[CH:4][CH:3]=1>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:17]=[O:18])=[CH:10][C:11]([N:14]([CH3:15])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

参加物

3

反応物 1

HCID 59266574(4'-Bromo-4-(dimethylamino)biphenyl-2-yl)methanol

生成物 1

HCID 592665494'-Bromo-4-(dimethylamino)biphenyl-2-carbaldehyde収率 70%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
40 °C

実験手順

IBX (3.29 g, 11.76 mmol) was added to a solution of (4′-bromo-4-(dimethylamino)biphenyl-2-yl)methanol (1.8 g, 5.88 mmol) in dmso (50 mL) and stirred at 40° C. for 3 hours. The reaction was diluted with water and extracted with diethyl ether. The ether layer was dried over MgSO4, filtered and evaporated to give the crude material. The crude product was purified on the Biotage (5-20% EtOAc:Hex) to give 4′-bromo-4-(dimethylamino)biphenyl-2-carbaldehyde (1.25 g, 4.11 mmol, 70% yield) as a yellow solid. 1H NMR (500 MHz, CHLOROFORM-d) δ 2.95-3.13 (m, 6H) 7.01 (dd, J=8.55, 3.05 Hz, 1H) 7.22 (m, 2H) 7.28-7.33 (m, 2H) 7.57 (m, 2H) 9.96 (s, 1H).

後処理

  1. extractionextracted with diethyl ether
  2. dry with materialThe ether layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give the crude material
  6. customThe crude product was purified on the Biotage (5-20% EtOAc:Hex)

出典と根拠

ORDレコード
ord-4974b1aeb3d0461487574852b37b97d4
出典データセット
uspto-grants-2013_10
特許番号
US08563505B2

反応ノート

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