Benzyl Bromide → 1-benzyl-1H-imidazole-2-carbaldehyde

HRID 908037

反応式

HRID 908037 の反応式
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH2:15]([N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 249551H-imidazole-2-carbaldehyde

生成物 1

HCID 1390821-benzyl-1H-imidazole-2-carbaldehyde収率 96.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
40 °C

実験手順

To a solution of 1H-imidazole-2-carbaldehyde (240 mg, 2.4 mmol) and potassium carbonate (662 mg, 4.8 mmol) in acetonitrile (5 mL) at 0° C. was added dropwise (bromomethyl)benzene (493 mg, 2.88 mmol). The mixture was stirred at 40° C. for 4 hr. Then the mixture was filtrated, evaporated to remove the acetonitrile from the filtrate, added EtOAc to extract the residues, and washed the extract with brine and water. The organic layer was dried with anhydrous Na2SO4, concentrated, and chromatographed on a silica gel column (EtOAc:hexane=1:9) to obtain the title compound (430 mg, yield 95%). LC-MS (ESI) m/z: 187 (M+1)+.

後処理

  1. filtrationThen the mixture was filtrated
  2. customevaporated
  3. customto remove the acetonitrile from the filtrate
  4. additionadded EtOAc
  5. extractionto extract the residues
  6. washwashed the
  7. extractionextract with brine and water
  8. dry with materialThe organic layer was dried with anhydrous Na2SO4
  9. concentrationconcentrated
  10. customchromatographed on a silica gel column (EtOAc:hexane=1:9)

出典と根拠

ORDレコード
ord-96af5264065d4c51bae7604ec49976ea
出典データセット
uspto-grants-2011_09
特許番号
US08012976B2

関連ノート

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