Ammonium Chloride → 5-Bromo-2-(4-methanesulfonylbenzyloxy)pyridine

HRID 42142

反応式

HRID 42142 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][S:10]([C:13]1[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1)(=[O:12])=[O:11].CC(C)([O-])C.[K+].[Cl-].[NH4+]>O1CCCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:18][CH2:17][C:16]2[CH:15]=[CH:14][C:13]([S:10]([CH3:9])(=[O:12])=[O:11])=[CH:20][CH:19]=2)=[N:3][CH:4]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 693532,5-DibromopyridineHCID 3801026(4-Methanesulfonylphenyl)methanolHCID 23665647Potassium tert-butoxide

生成物 1

HCID 670832565-Bromo-2-(4-methanesulfonylbenzyloxy)pyridine収率 31%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 2,5-dibromopyridine (474 mg, 2.00 mmol) and 4-(methanesulfonyl)benzyl alcohol (372 mg, 2.00 mmol) in tetrahydrofuran (5 mL) was cooled to −15° C. under N2 and potassium tert-butoxide (1.0M in tetrahydrofuran, 2.2 mL, 2.20 mmol) was added dropwise over 10 minutes. The mixture was stirred at 0° C. for 5.5 hours, poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (210 mg, yield 31%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

出典と根拠

ORDレコード
ord-c78bc94182cb42c48b59f4800f97a3c8
出典データセット
uspto-grants-2013_09
特許番号
US08536176B2

関連ノート

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