2'-Nitroacetophenone → 2-Bromo-2'-nitroacetophenone

HRID 1194054Notes

Reaction equation

HRID 1194054 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:12])[CH3:11])([O-:3])=[O:2].[Cl-].[Al+3].[Cl-].[Cl-].[Br:17]Br>CCOCC>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:12])[CH2:11][Br:17])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 113462'-NitroacetophenoneHCID 24408BromineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2440252-Bromo-2'-nitroacetophenoneYield 77.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

o-Nitroacetophenone (8.3 g, 50 mmol) in ether (100 ml) was treated with aluminium chloride (catalytic amount) followed by bromine (2.55 ml, 50 mmol) over 10 mins and the reaction stirred for 30 mins. The reaction was quenched with aqueous sodium bicarbonate, the ether layer separated, dried (MgSO4) and evaporated under reduced pressure. The residue was taken up in ethyl acetate, the solution was dried (MgSO4), and evaporated under reduced pressure to yield o-nitro phenacyl bromide as a yellow oil (9.45 g, 77%); δH (CDCl3) 7.2-8.35 (4H, m, aryl), 4.30 (2H, S, CH2).

Workup

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. customthe ether layer separated
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. dry with materialthe solution was dried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-467bc9a4113f4a7f9316e852da793473
Source dataset
uspto-grants-1989_03
Patent number
US04812470

Reaction notes

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