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

HRID 273996

반응식

HRID 273996 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-260917c3a7ef4014bb2b71352417c94a
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387685

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