Borane → 3-Bromo-5-methoxybenzenemethanamine

HRID 1614973노트

반응식

HRID 1614973 반응식
[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

참가 물질

4

반응물 2

HCID 6331BoraneHCID 250673623-Bromo-5-methoxybenzonitrile

생성물 1

HCID 534144413-Bromo-5-methoxybenzenemethanamine수율 19.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e3acce5bc11b4d48837af5410db73ba2
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765727B2

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