Methyl iodide → Methyl 2-amino-5-bromo-3-methylbenzoate

HRID 2284584Notes

Reaction equation

HRID 2284584 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13]([O-])([O-])=O.[Cs+].[Cs+].IC>CN(C=O)C.O>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 118503832-Amino-5-bromo-3-methylbenzoic acid

Product 1

HCID 2763413Methyl 2-amino-5-bromo-3-methylbenzoateYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

2-Amino-5-bromo-3-methylbenzoic acid (5.0 g, 21.7 mmol) in dry DMF (35 mL) was stirred with Cs2CO3 (10.62 g, 32.6 mmol) at room temperature for 1 h under nitrogen. Iodomethane (3.4 g, 1.5 mL, 23.95 mmol) in dry DMF (7 ml) was added dropwise to the above stirring reaction mixture over a period of 30 min and continued the reaction for 24 h. Reaction mixture was diluted with water (200 mL) and stirred to observe hetergeneous suspension. The purple solid was collected by filtration and dried to obtain methyl 2-amino-5-bromo-3-methylbenzoate (4.72 g, 89%). 1H NMR (DMSO-d6): δ 7.67 (app d, 1H, J=2.1 Hz), 7.34 (s, 1H), 6.60 (s, 2H), 3.78 (s, 3H), 2.09 (s, 3H).LCMS: rt 7.98 min (A), purity 99%, MS (m/e) 245 (MH+).

Workup

  1. customreaction mixture over a period of 30 min
  2. customthe reaction for 24 h
  3. customReaction mixture
  4. stirringstirred
  5. filtrationThe purple solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-8048229c21674b33aba051b6813a27ee
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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