4-[2-(Tert-butyldimethylsilanyloxy)ethoxy]bromobenzene → 5-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-benzoyl}-2-chloro-benzenesulfonamide

HRID 873641ノート

反応式

HRID 873641 の反応式
Br[C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.C([Li])CCC.[Cl:24][C:25]1[CH:36]=[CH:35][C:28]([C:29](N(OC)C)=[O:30])=[CH:27][C:26]=1[S:37](=[O:40])(=[O:39])[NH2:38]>O1CCCC1>[C:13]([Si:10]([CH3:12])([CH3:11])[O:9][CH2:8][CH2:7][O:6][C:5]1[CH:17]=[CH:18][C:2]([C:29]([C:28]2[CH:35]=[CH:36][C:25]([Cl:24])=[C:26]([S:37]([NH2:38])(=[O:39])=[O:40])[CH:27]=2)=[O:30])=[CH:3][CH:4]=1)([CH3:16])([CH3:15])[CH3:14]

参加物

5

反応物 3

HCID 150978074-[2-(Tert-butyldimethylsilanyloxy)ethoxy]bromobenzeneHCID 581073994-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamideHCID 178418339Butyllithium

生成物 1

HCID 668504935-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-benzoyl}-2-chloro-benzenesulfonamide収率 53.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

[2-(4-Bromo-phenoxy)-ethoxy]-tert-butyl-dimethyl-silane (7.3 g, 22.12 mmol) is dissolved in tetrahydrofuran (120 mL) and cooled to −78° C. The solution is treated with a solution of n-butyllithium (1.6 M in hexanes, 13.8 mL, 22.12 mmol) and stirred 30 minutes after which a solution of 4-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamide (2.05 g, 7.37 mmol) in tetrahydrofuran (20 mL) is added. The reaction is allowed to stir for 18 hours while warming to ambient temperature. The reaction is quenched with a saturated solution of ammonium chloride and extracted twice with ether. The organic phase is separated and concentrated in vacuo. The residue is purified by column chromatography (gradient of ethyl acetate in hexanes 10-50%) affording 1.84 g (53% yield) of the title compound. MS (m/z): 470.2 (M+1).

後処理

  1. additionis added
  2. temperaturewhile warming to ambient temperature
  3. customThe reaction is quenched with a saturated solution of ammonium chloride
  4. extractionextracted twice with ether
  5. customThe organic phase is separated
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by column chromatography (gradient of ethyl acetate in hexanes 10-50%)

出典と根拠

ORDレコード
ord-1c953be737014c299effa3bbf792dfc8
出典データセット
uspto-grants-2015_03
特許番号
US08975439B2

反応ノート

読み込み中…