Borane → 3-Bromo-5-methoxybenzenemethanamine

HRID 1614973ノート

反応式

HRID 1614973 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[C:5]#[N:6].B>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][NH2:6])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

参加物

4

反応物 2

HCID 6331BoraneHCID 250673623-Bromo-5-methoxybenzonitrile

生成物 1

HCID 534144413-Bromo-5-methoxybenzenemethanamine収率 19.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
70 °C

実験手順

3-Bromo-5-methoxybenzonitrile (13.1 g, 61.8 mmol) was dissolved in dry tetrahydrofuran (100 mL) in a flame-dried flask and cooled in an ice bath. A solution of borane in tetrahydrofuran (100 mL, 0.10 mol, 1.0 M) was slowly added over a period of 30 minutes. After the addition was complete, the mixture was heated at 70° C. overnight and quenched slowly with ice water and Na2CO3 (saturated aqueous solution). After removal of THF, the residue was extracted with large amounts of EtOAc three times. The combined organic layers were washed with water, dried, and concentrated to give the crude product, which was purified by silica gel column chromatography to give the desired product as a white powder (2.57 g, 19%). LCMS for C8H10BrNO (M+H)+: m/z=216.9, 218.9.

後処理

  1. temperaturecooled in an ice bath
  2. additionAfter the addition
  3. customquenched slowly with ice water and Na2CO3 (saturated aqueous solution)
  4. customAfter removal of THF
  5. extractionthe residue was extracted with large amounts of EtOAc three times
  6. washThe combined organic layers were washed with water
  7. customdried
  8. concentrationconcentrated
  9. customto give the crude product, which
  10. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-e3acce5bc11b4d48837af5410db73ba2
出典データセット
uspto-grants-2014_07
特許番号
US08765727B2

反応ノート

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