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

HRID 2168311

反応式

HRID 2168311 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4263e9ef95164dd0930c99abca3b5606
出典データセット
uspto-grants-2015_06
特許番号
US09045500B2

関連ノート

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