4-Bromo-2-chlorobenzonitrile → (4-Bromo-2-chlorophenyl)methanamine

HRID 219166

反応式

HRID 219166 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([Cl:10])[CH:3]=1

参加物

3

反応物 1

HCID 70104204-Bromo-2-chlorobenzonitrile

生成物 1

HCID 25258775(4-Bromo-2-chlorophenyl)methanamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
23 °C

実験手順

To a solution of 4-bromo-2-chlorobenzonitrile (2500 mg, 11549 μmol) in THF (20 mL) at 0° C. was added borane-methyl sulfide complex, 2.0 m sol in THF (28873 μl, 57747 μmol). Ice bath removed and reaction stirred overnight warming to 23° C. Reaction cooled to 0° C. and quenched with MeOH (15 mL). Reaction then partitioned between CHCl3 (100 mL) and 1M NaOH (100 mL). Organic dried with brine and MgSO4. Organic then concentrated to an oil under reduced pressure and purified on silica (80 g) eluting with 0>6% 2M NH3 in MeOH/DCM and product isolated as a colorless oil. MS (ESI pos. ion) m/z: 220/222 (MH+). Calc'd exact mass for C7H7BrClN: 219/221

後処理

  1. customIce bath removed
  2. customreaction
  3. customReaction
  4. temperaturecooled to 0° C.
  5. customquenched with MeOH (15 mL)
  6. customReaction
  7. customthen partitioned between CHCl3 (100 mL) and 1M NaOH (100 mL)
  8. dry with materialOrganic dried with brine and MgSO4
  9. concentrationOrganic then concentrated to an oil under reduced pressure
  10. custompurified on silica (80 g)
  11. washeluting with 0>6% 2M NH3 in MeOH/DCM and product
  12. customisolated as a colorless oil

出典と根拠

ORDレコード
ord-253495461d894022a97902c47499aa45
出典データセット
uspto-grants-2012_06
特許番号
US08198448B2

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