Hydrochloric Acid → 3-(Bromomethyl)aniline

HRID 1256146Notes

Reaction equation

HRID 1256146 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[CH:4]=1.Cl>CCO.[Fe]>[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[NH2:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 212573253-(Bromomethyl)anilineYield 89.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred suspension of 1-(bromomethyl)-3-nitrobenzene (40 g; 0.18 mol) and iron powder (31 g; 0.55 mol) in EtOH (1000 mL) was added concentrated HCl (33.8 g, 0.93 mol) at r.t. The mixture was stirred at 85° C. for 2 hrs, cooling to r.t. and filtered. The filtrate was evaporated and the residue was solved in EtOAc and washed with brine, dried (Na2SO4) and concentrated to give the 3-(bromomethyl)aniline (30 g, 87% yield) as a yellow solid. 1H NMR: (400 MHz, MeOD) δ 7.59-7.56 (m, 1H), 7.54 (t, 1H), 7.39 (d, 1H), 7.38-7.34 (m, 1H), 4.73 (s, 2H).

Workup

  1. temperaturecooling to r.t.
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dc275b6f07bc42a3b5857e4c5e4beeb1
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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