Boron tribromide → 2-Amino-3-hydroxybenzonitrile

HRID 471619ノート

反応式

HRID 471619 の反応式
[NH2:1][C:2]1[C:9]([O:10]C)=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 118191992-amino-3-methoxybenzonitrile

生成物 1

HCID 159063362-Amino-3-hydroxybenzonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 2-amino-3-methoxybenzonitrile (Example 127b) (0.98 g, 6.59 mmol) in CH2Cl2 (25.0 mL), a solution of BBr3 in CH2Cl2 (1.0M, 19.8 mL, 19.77 mmol) was added drop wise at −78° C. under a nitrogen atmosphere. The obtained mixture was stirred at −78° C. for 30 min, and then at room temperature overnight. The reaction was quenched with water, basified with saturated aqueous NaHCO3 (pH˜8) and extracted with CH2Cl2. The combined extract was dried with MgSO4, filtered and evaporated. The title compound was obtained in amount of 0.80 g (91%) as orange solid and was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 9.86 (broad s, 1H), 6.82-6.87 (m, 2H), 6.46 (t, J=8.0 Hz, 1H), 5.34 (broad s, 2H).

後処理

  1. customat room temperature
  2. customovernight
  3. customThe reaction was quenched with water
  4. extractionextracted with CH2Cl2
  5. extractionThe combined extract
  6. dry with materialwas dried with MgSO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-b8ecc2f5e83542b0ba304376338601ac
出典データセット
uspto-grants-2014_01
特許番号
US08633186B2

反応ノート

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