Borane → (2-Bromo-5-methoxyphenyl)methanamine

HRID 1614967

Reaction equation

HRID 1614967 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[C:4]#[N:5].B>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH2:4][NH2:5]

Participants

4

Reactant 2

HCID 6331BoraneHCID 217840962-Bromo-5-methoxybenzonitrile

Product 1

HCID 24691009(2-Bromo-5-methoxyphenyl)methanamineYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Bromo-5-methoxybenzonitrile (10.0 g, 47.2 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 (75 mL, 75 mmol, 1.0 M) was added dropwise over a period of 30 minutes. The reaction mixture was stirred overnight at rt, then 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, which was purified by silica gel column chromatography to give the desired product as a white powder (3.65 g, 36%). LCMS for C8H10BrNO (M+H)+: m/z=216.9, 219.0.

Workup

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

Sources & evidence

ORD record
ord-16a1b52403504369b3559284ecc970ba
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Linked notes

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