3-(Bromomethyl)benzoic acid → 3-[2-Cyano-2-(3,4-dimethoxyphenyl)-2-[(4-methylphenyl)thio]ethyl]benzoic acid

HRID 273996

反応式

HRID 273996 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([Li])CCC.[C:27]([C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33]Br)([OH:29])=[O:28]>O1CCCC1.CCCCCC>[C:12]([C:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)([S:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)[CH2:33][C:32]1[CH:31]=[C:30]([CH:37]=[CH:36][CH:35]=1)[C:27]([OH:29])=[O:28])#[N:13]

参加物

6

反応物 3

HCID 2456503-(Bromomethyl)benzoic acidHCID 105421673,4-Dimethoxy-alpha[(4-methylphenyl)thio]benzeneacetonitrileHCID 178418339Butyllithium

生成物 1

HCID 105988973-[2-Cyano-2-(3,4-dimethoxyphenyl)-2-[(4-methylphenyl)thio]ethyl]benzoic acid収率 85.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

To a cold (-78° C.) solution of 1.86 g of 3,4-dimethoxy-α-[(4-methylphenyl)thio]benzene acetonitrile in 15 mL of tetrahydrofuran is added drop-wise a solution of 2.9 mL of n-butyl lithium (2.2 M) in hexane. This solution is stirred at -78° C. for 35 minutes. A solution of 0.67 g of m-carboxybenzyl bromide in 5 mL of anhydrous tetrahydrofuran is added drop-wise, stirred at -78° C. for 40 minutes and then at room temperature for 15 minutes. The mixture is quenched with water and extracted with ethyl acetate. The ethyl acetate extract is washed with brine, dried and filtered. The filtrate is evaporated in vacuo to yield a yellow oil. This oil is purified by flash chromatography using methylene chloride/methyl alcohol (95:5) to yield 1.15 g of the desired product as a yellow foam.

後処理

  1. stirringstirred at -78° C. for 40 minutes
  2. waitat room temperature for 15 minutes
  3. customThe mixture is quenched with water
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washis washed with brine
  7. customdried
  8. filtrationfiltered
  9. customThe filtrate is evaporated in vacuo
  10. customto yield a yellow oil
  11. customThis oil is purified by flash chromatography

出典と根拠

ORDレコード
ord-260917c3a7ef4014bb2b71352417c94a
出典データセット
uspto-grants-1995_02
特許番号
US05387685

関連ノート

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