Water → Benzonitrile, 3-bromo-4-hydroxy-5-nitro-

HRID 1430775

反応式

HRID 1430775 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](Br)[C:9]=1[OH:10])[C:5]#[N:6].[N:12]([O-:14])=[O:13].[Na+].BrBr.O>C(O)(=O)C.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[C:9]=1[OH:10])[C:5]#[N:6]

参加物

7

反応物 4

HCID 962WaterHCID 15531BromoxynilHCID 24408BromineHCID 23668193Sodium Nitrite

生成物 1

HCID 3014048Benzonitrile, 3-bromo-4-hydroxy-5-nitro-収率 84.2%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

(I1B): To a suspension of 3,5-dibromo-4-hydroxybenzonitrile (2.11 g, 7.62 mmol) in acetic acid (70 mL) was added sodium nitrite (2.63 g, 38.1 mmol) in small portion, evolving bubbles and bromine were observed. After addition, the mixture was stirred at 50° C. overnight. Reaction was cooled to room temperature; water (250 mL) was added and extracted with EtOAc for two times. The combined extracts were washed with water and brine, dried over MgSO filtered and the filtrate was concentrated to give yellow orange solid. The solid was treated with small amount of MeOH, collected by filtration, rinsed with MeOH, dried to afford 1.56 g of 3-bromo-4-hydroxy-5-nitrobenzonitrile as yellow solid.

後処理

  1. additionAfter addition
  2. customReaction
  3. temperaturewas cooled to room temperature
  4. extractionextracted with EtOAc for two times
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over MgSO
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customto give yellow orange solid
  10. filtrationcollected by filtration
  11. washrinsed with MeOH
  12. customdried

出典と根拠

ORDレコード
ord-6b3ae8118292419f878aed71c13b7ad8
出典データセット
uspto-grants-2015_01
特許番号
US08940736B2

関連ノート

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