Boron tribromide → 3,4-Dihydroxy-5-nitrobenzaldehyde

HRID 2570

반응식

HRID 2570 반응식
[N+:1]([C:4]1[C:5]([OH:14])=[C:6]([O:12]C)[CH:7]=[C:8]([CH:11]=1)[CH:9]=[O:10])([O-:3])=[O:2].B(Br)(Br)Br>ClCCl>[N+:1]([C:4]1[CH:11]=[C:8]([CH:7]=[C:6]([OH:12])[C:5]=1[OH:14])[CH:9]=[O:10])([O-:3])=[O:2]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 811345-Nitrovanillin

생성물 1

HCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde수율 55.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

35 g of 5-nitro vanillin (commercial) and 1200 ml of dichloromethane were mixed together under nitrogen and the mixture was cooled to 0° C. 533 ml of a molar solution of boron tribromide in dichloromethane were added and the mixture stood for 2 days at abmient temperature and then was concentrated. The residue was taken up cold (ice bath+methanol) in 300 ml of 2N hydrochloric acid and the mixture was stirred for two to three hours at this temperature, then left for 16 hours at ambient temperature. Extraction was carried out with ethyl acetate and the organic phase was washed, dried and concentrated to obtain 18 g of the expected product melting at >260° C.

후처리

  1. concentrationwas concentrated
  2. waitleft for 16 hours at ambient temperature
  3. extractionExtraction
  4. washthe organic phase was washed
  5. customdried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9efe6333e98c4733b21ed3413c8658d8
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728828

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