Methanol → HCID 71743654, compound

HRID 2277610Notes

Reaction equation

HRID 2277610 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].[CH:11]1([Mg]Br)[CH2:13][CH2:12]1.CO.[BH4-].[Na+]>C1COCC1.CCOC(C)=O.O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH:4]([CH:11]1[CH2:13][CH2:12]1)[NH2:5]

Participants

8

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 103309442-Bromo-5-chlorobenzonitrileHCID 178418630HCID 178418630, compound

Product 1

HCID 71743654HCID 71743654, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-5-chlorobenzonitrile (20 g, 93 mmol) in THF (200 mL) was added cyclopropylmagnesiumbromide (558 mL, 279 mmol) at 0° C. The resulting reaction mixture was stirred at 0-5° C. for 5 hours before MeOH (100 mL) was added and stirring continued at room temperature for 15 min. NaBH4 (7.1 g, 186 mmol) was added subsequently and the reaction mixture was stirred at room temperature overnight. Water was added and reaction mixture was exacted with AcOEt (300 mL×3). The combined organic layers were concentrated in vacuo to give a crude product which was then purified by chromatography to give (2-bromo-5-chlorophenyl)(cyclopropyl)methanamine (8.2 g, yield 34%).

Workup

  1. customThe resulting reaction mixture
  2. additionwas added
  3. stirringthe reaction mixture was stirred at room temperature overnight
  4. customreaction mixture
  5. concentrationThe combined organic layers were concentrated in vacuo
  6. customto give a crude product which
  7. customwas then purified by chromatography

Sources & evidence

ORD record
ord-985771a8ee8248cfae7dbb82a140f0da
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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