Ethyl Acetate → 1-(2-Amino-5-bromophenyl)ethan-1-one

HRID 1816871Notes

Reaction equation

HRID 1816871 reaction equation
[Br:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([NH2:11])=[CH:4][CH:3]=1.C[Li].[Cl-].[NH4+].[C:16](OCC)(=O)C>C1COCC1>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:10][C:6]=1[C:7](=[O:9])[CH3:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 798582-Amino-5-bromobenzoic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 110747461-(2-Amino-5-bromophenyl)ethan-1-oneYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo anthranilic acid (50 g, 0.231 mol) in anhydrous THF (500 mL) at 0° C. under nitrogen was added in a dropwise manner methyllithium (1.4 M in diethyl ether, 661 mL, 0.926 mol). After addition, the reaction mixture was slowly allowed to warm to room temperature, stirred overnight, and treated with aqueous saturated ammonium chloride solution (1000 mL). Ethyl acetate (400 mL) was added and organic layer was separated. The aqueous layer was extracted with ethyl acetate (3×200 mL). The combined organic layers were dried (Mg2SO4) and concentrated. The residue was purified by a flash chromatography on silica gel (hexane:ethyl acetate/9:1) to afford the title compound as a brown solid (29.3 g, 59%). MS (ES) m/z 214/216 ([M+H]+, 100%).

Workup

  1. additionAfter addition
  2. customorganic layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×200 mL)
  4. dry with materialThe combined organic layers were dried (Mg2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by a flash chromatography on silica gel (hexane:ethyl acetate/9:1)

Sources & evidence

ORD record
ord-f456b31069a24f63b8c86bffd28a0042
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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