Triethylamine → Methyl 3-(2-bromo-3,5-difluorophenyl)propanoate

HRID 625696

反応式

HRID 625696 の反応式
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[Br:10].[CH3:11][O:12][CH:13]([O:16]C)[CH:14]=[CH2:15].C(N(CC)CC)C>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[Br:10][C:3]1[C:4]([F:9])=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[CH2:15][CH2:14][C:13]([O:12][CH3:11])=[O:16]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 80145Acrolein dimethyl acetalHCID 27245171,2-Dibromo-3,5-difluorobenzene

生成物 1

HCID 89826041Methyl 3-(2-bromo-3,5-difluorophenyl)propanoate

試薬・触媒・溶媒 2

HCID 70681Tetrabutylammonium Chloride触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 1,2-dibromo-3,5-difluorobenzene (4.5 g), 3,3-dimethoxyprop-1-ene (5.1 mL), tetrabutylammonium chloride (4.6 g) and triethylamine (3.5 mL) in N,N-dimethylformamide (50 mL) is purged with nitrogen for 20 minutes. Palladium-(II)-acetate (111 mg) is added and the mixture heated for 16 hours at 90° C. After cooling the mixture is partitioned between aqueous HCl (1 M) and diethyl ether, the organic layer dried (Na2SO4), volatiles evaporated under reduced pressure and the residue purified by column chromatography (silica gel; hexane:ethyl acetate 98:2→80:20) to give the title compound (Yield 3.6 g).

後処理

  1. customis purged with nitrogen for 20 minutes
  2. additionPalladium-(II)-acetate (111 mg) is added
  3. temperatureAfter cooling the mixture
  4. customis partitioned between aqueous HCl (1 M) and diethyl ether
  5. dry with materialthe organic layer dried (Na2SO4)
  6. customvolatiles evaporated under reduced pressure
  7. customthe residue purified by column chromatography (silica gel; hexane:ethyl acetate 98:2→80:20)

出典と根拠

ORDレコード
ord-8f53b8bc5e954936a05f94d1a5e40149
出典データセット
uspto-grants-2016_04
特許番号
US09308194B2

関連ノート

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