3-Chlorobenzaldehyde → (4-Bromo-2,5-dichloro-3-thienyl)(3-chlorophenyl)methanol

HRID 870047ノート

反応式

HRID 870047 の反応式
Br[C:2]1[C:6]([Br:7])=[C:5]([Cl:8])[S:4][C:3]=1[Cl:9].[Li]CCCC.[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=[O:20]>C1COCC1>[Br:7][C:6]1[C:2]([CH:19]([C:18]2[CH:21]=[CH:22][CH:23]=[C:16]([Cl:15])[CH:17]=2)[OH:20])=[C:3]([Cl:9])[S:4][C:5]=1[Cl:8]

参加物

5

反応物 3

HCID 114773-ChlorobenzaldehydeHCID 70153183,4-Dibromo-2,5-dichlorothiopheneHCID 178418339Butyllithium

生成物 1

HCID 57900988(4-Bromo-2,5-dichloro-3-thienyl)(3-chlorophenyl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 3,4-dibromo-2,5-dichlorothiophene (2.00 g, 6.43 mmol) in THF (18 mL) at −78° C., was added n-BuLi (2.5M in hexane, 2.57 mL, 6.43 mmol) dropwise. After 30 min., 3-chlorobenzaldehyde (0.732 mL, 6.43 mmol) was added dropwise to the yellow solution. The resulting solution was stirred at −78° C. for 30 min. and allowed to warm to 0° C. After 30 min., the reaction was quenched by the addition of 25% aq. NH4OAc. The aqueous layer was extracted with EtOAc and the combined organics were washed with water and brine, dried (Na2SO4) and concentrated. The crude product was purified by chromatography on silica gel (50:50 to 80:20 CHCl3/hexane) to afford the desired product as a pale yellow oil.

後処理

  1. temperatureto warm to 0° C
  2. waitAfter 30 min.
  3. customthe reaction was quenched by the addition of 25% aq. NH4OAc
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe combined organics were washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography on silica gel (50:50 to 80:20 CHCl3/hexane)

出典と根拠

ORDレコード
ord-5ec3e8f4ff7345f4b17b6326447c023e
出典データセット
uspto-grants-2015_03
特許番号
US08969394B2

反応ノート

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