Sodium Hydroxide → 6-Bromo-2-fluoropyridin-3-ol

HRID 335952ノート

反応式

HRID 335952 の反応式
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[Na+].[Br:11]Br.S([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.CCOC(C)=O.O>[Br:11][C:4]1[N:3]=[C:2]([F:1])[C:7]([OH:8])=[CH:6][CH:5]=1

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 24437Sodium SulfiteHCID 27627852-Fluoro-3-hydroxypyridine

生成物 1

HCID 299198756-Bromo-2-fluoropyridin-3-ol収率 36.3%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-Fluoropyridin-3-ol (5.96 g, 52.7 mmol) was suspended in acetic acid and cooled in an ice bath. NaOH (10.0 N, 6.0 mL, 60.0 mmol) was added and the mixture stirred for 10 min. Bromine (2.8 mL, 54.4 mmol) was added dropwise and the mixture stirred for 20 min. Sodium sulfite (1.4 g) was added and the mixture stirred for 10 min. Water (400 mL) and EtOAc (400 mL) were added and the phases mixed and separated. The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (hexane to ethyl acetate gradient) gave the desired 6-bromo-2-fluoropyridin-3-ol (3.67 g, 19.12 mmol, 36.3% yield) MS m/z=192.0, 194.0 [M+H]+. Calculated for C5H3BrFNO: 190.94.

後処理

  1. temperaturecooled in an ice bath
  2. stirringthe mixture stirred for 20 min
  3. stirringthe mixture stirred for 10 min
  4. additionthe phases mixed
  5. customseparated
  6. dry with materialThe organic was dried with magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. customPurification

出典と根拠

ORDレコード
ord-2dfd1a72bb654e8fa0524e3d30875bee
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

反応ノート

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