Acetic Acid → N-benzyl-4-bromoaniline

HRID 270030Notes

Reaction equation

HRID 270030 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>ClC(Cl)C>[CH2:9]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 78074-BromoanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 961575N-benzyl-4-bromoanilineYield 84.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 4-bromoaniline (1.76 g, 10 mmol) and benzaldehyde (1.06 g, 10 mmol) in dichloroethane (15 mL) was treated with NaBH(OAc)3 (2.32 g, 11 mmol) and glacial acetic acid (1 mL), stirred overnight at room temperature, quenched with 1N NaOH, and extracted with CH2Cl2 (3×50 mL). The combined extracts were washed with water and brine, dried, (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5:1 hexanes/ethyl acetate to provide 2.21 g (84%) of the desired product. MS (ESI) m/e 261.9 (M+H)+, 263.9 (M+H)+.

Workup

  1. customquenched with 1N NaOH
  2. extractionextracted with CH2Cl2 (3×50 mL)
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried, (Na2SO4),
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 5:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-9052342919aa46929a2ba4601815ad2f
Source dataset
uspto-grants-2008_11
Patent number
US07449485B2

Reaction notes

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