Acetone → 1-Bromo-3-(3-fluoro-2-methyl-phenyl)-propan-2-one

HRID 1963090ノート

反応式

HRID 1963090 の反応式
[Br:1]Br.[F:3][C:4]1[C:5]([CH3:14])=[C:6]([CH2:10][C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][CH:9]=1.Br.CC(C)=O>C(O)(=O)C>[Br:1][CH2:12][C:11](=[O:13])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([F:3])[C:5]=1[CH3:14]

参加物

6

反応物 4

HCID 180AcetoneHCID 260Hydrogen BromideHCID 24408BromineHCID 247216491-(3-Fluoro-2-methylphenyl)propan-2-one

生成物 1

HCID 866706671-Bromo-3-(3-fluoro-2-methyl-phenyl)-propan-2-one収率 69.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒3 回

実験手順

Analogously to the procedure described in H. Y. Choi et al., Org. Lett. 5 (2003), 411, a solution of bromine (8.46 g, 52.95 mmol) in acetic acid (12 ml) was added at 0° C. to a solution of 1-(3-fluoro-2-methyl-phenyl)-propan-2-one (4.00 g, 24.07 mmol) in acetic acid (4 ml) and a 33% solution of hydrogen bromide in acetic acid (4 ml). The mixture was warmed to room temperature and stirred for 12 h. Then acetone was added and the mixture was stirred for 24 h. After evaporation under reduced pressure, the residue was extracted several times with DCM. The combined extracts were dried over sodium sulfate and evaporated to dryness. The residue was purified by preparative HPLC to give 4.10 g of the title compound as an oil.

後処理

  1. stirringthe mixture was stirred for 24 h
  2. customAfter evaporation under reduced pressure
  3. extractionthe residue was extracted several times with DCM
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-e995ad2801044255bf33f9df0d108906
出典データセット
uspto-grants-2013_04
特許番号
US08415336B2

反応ノート

読み込み中…