N-Iodosuccinimide → Methyl 2-amino-5-bromo-3-iodobenzoate

HRID 1678245Notes

Reaction equation

HRID 1678245 reaction equation
[I:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]>FC(F)(F)C(O)=O>[NH2:9][C:10]1[C:19]([I:1])=[CH:18][C:17]([Br:20])=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 736224Methyl 2-amino-5-bromobenzoate

Product 1

HCID 53435544Methyl 2-amino-5-bromo-3-iodobenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-Iodo-pyrrolidine-2,5-dione (10.35 g, 46.0 mmol) was added in one portion to a solution of methyl 2-amino-5-bromo-benzoate (10.35 g, 45.0 mmol) in trifluoroacetic acid (90 mL) at ambient temperature. The reaction was stirred for about 1 hour at ambient temperature then concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (150 mL), washed with saturated Na2CO3 solution (2×150 mL) and a 10% aqueous solution of Na2S2O4 (2×100 mL), dried over anhydrous MgSO4, filtered and concentrated to yield methyl 2-amino-5-bromo-3-iodo-benzoate (15.5 g, 97%) as a yellow solid; RP HPLC (Table 1, Method e) Rt=2.45, 1H NMR (DMSO-d6, 400 MHz) δ 3.83 (s, 3H), 7.74 (broad s), 2H), 7.86-7.88 (d, 2H), 8.00-8.02 (d, 1H).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2 (150 mL)
  3. washwashed with saturated Na2CO3 solution (2×150 mL)
  4. dry with materiala 10% aqueous solution of Na2S2O4 (2×100 mL), dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7538d8eecaf24a5d92cce2982de97049
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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