Acetic Acid → N-Benzyl-3-bromoaniline

HRID 386473Notes

Reaction equation

HRID 386473 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)(=O)C.[BH4-].[Na+]>O1CCCC1>[CH2:9]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([Br:1])[CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 115623-BromoanilineHCID 4311764Sodium borohydride

Product 1

HCID 9965096N-Benzyl-3-bromoaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromo aniline (5 g, 29 mmol), benzaldehyde (3.24 ml, 32 mmol) and acetic acid (2.49 ml, 44 mmol) in dry tetrahydrofuran (50 ml) was stirred at room temperature for 3 hrs. Sodium borohydride (2.755 g, 73 mmol) was added and the reaction stirred at room temperature overnight. The reaction mixture was quenched with water (100 ml) and extracted with dichloromethane (3×100 ml). The organic extracts were combined, dried (magnesium sulphate) and concentrated in vacuo. HPLC retention time 7.7 min. Mass spectrum (ES+) m/z 263 (M+H)

Workup

  1. customThe reaction mixture was quenched with water (100 ml)
  2. extractionextracted with dichloromethane (3×100 ml)
  3. dry with materialdried (magnesium sulphate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f59f3517fb846b48b28bfbaacf39367
Source dataset
uspto-grants-2013_02
Patent number
US08372840B2

Reaction notes

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