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

HRID 587251노트

반응식

HRID 587251 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric Acid2회HCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 124330084-(Bromomethyl)naphthalene-1-carbonitrile

생성물 1

HCID 109119034-(Bromomethyl)-1-naphthaldehyde수율 88%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

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]+).

후처리

  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)

출처 및 근거

ORD 기록
ord-60e705ad11b742a7a0f815eb374f1ad6
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226500B2

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