Formaldehyde → 6-bromo-2-methylene-2,3-dihydro-1H-inden-1-one

HRID 2168311

반응식

HRID 2168311 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.C=O.[C:14]1(B(O)O)C=CC=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[CH2:14])[C:8]2=[O:11])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 66827Phenylboronic AcidHCID 1397781-Indanone, 6-bromo-

생성물 1

HCID 581971666-bromo-2-methylene-2,3-dihydro-1H-inden-1-one수율 30%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 6-bromo-2,3-dihydro-1H-inden-1-one (0.3 g, 1.36 mmol), paraformaldehyde (0.4 g, 13.6 mmol), phenylboronic acid (0.2 g, 1.64 mmol) and trifluoroacetic acid (0.1 mL, 0.15 g, 1.36 mmol) in dry toluene (10 mL) was refluxed for 5 hours. When starting material was totally consumed, the crude mixture was cooled to room temperature, neutralized with saturated aqueous Na2CO3, extracted with ethyl acetate, dried and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, petroleum ether-ethyl acetate, 95:5) to give compound 6-bromo-2-methylene-2,3-dihydro-1H-inden-1-one (89 mg, 30%) as a white solid. 1H NMR (CDCl3, 400 MHz): 3.71 (s, 2H), 5.68 (s, 1H), 6.39 (s, 1H), 7.38-7.40 (d, 1H), 7.70-7.72 (d, 1H), 7.99 (s, 1H).

후처리

  1. customwas totally consumed
  2. extractionextracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (silica gel, petroleum ether-ethyl acetate, 95:5)

출처 및 근거

ORD 기록
ord-4263e9ef95164dd0930c99abca3b5606
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045500B2

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