Hydrochloric Acid → 4-(Bromomethyl)-1-naphthaldehyde

HRID 587251ノート

反応式

HRID 587251 の反応式
[Br:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]#N)=[CH:5][CH:4]=1.CC(C[AlH]CC(C)C)C.Cl.[OH2:25]>C1(C)C=CC=CC=1>[Br:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]=[O:25])=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 124330084-(Bromomethyl)naphthalene-1-carbonitrile

生成物 1

HCID 109119034-(Bromomethyl)-1-naphthaldehyde収率 88%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 4-(bromomethyl)-1-naphthonitrile (8 g, 33 mmol) in toluene (100 mL) at 0° C. was added dropwise DIBAL-H (1.0 M solution in toluene; 43 mL), and the reaction mixture was stirred at 0° C. for 1 h. 3 N HCl in water (50 mL) was added to the mixture until it became a white slurry and then additional 1 N HCl (20 mL) was added. The organic layer was collected and the aqueous layer was extracted with EtOAc (3 x100 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; 5% EtOAc in petroleum ether) afforded the title compound as a white solid (7 g, 88%): mp 115-116° C.; 1H NMR (400 MHz, CDCl3) δ 10.41 (s, 1H), 9.35 (m, 1H), 8.22 (m, 1H), 7.90 (d, J=8.0 Hz, 1H), 7.75 (m, 3H), 4.95 (s, 2H); ESIMS m/z 248.88 ([M+H]+).

後処理

  1. customThe organic layer was collected
  2. extractionthe aqueous layer was extracted with EtOAc (3 x100 mL)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (SiO2, 100-200 mesh; 5% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-60e705ad11b742a7a0f815eb374f1ad6
出典データセット
uspto-grants-2016_01
特許番号
US09226500B2

反応ノート

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