Ammonium Chloride → Methyl 2-bromo-4-carbamoylbenzoate

HRID 1037040Notes

Reaction equation

HRID 1037040 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5](O)=[O:6].[NH4+].[Cl-].C[N:18](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[NH2:18])[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 186730263-Bromo-4-(methoxycarbonyl)benzoic acid

Product 1

HCID 86685485Methyl 2-bromo-4-carbamoylbenzoateYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-bromo-4-(methoxycarbonyl)benzoic acid (2.5 g, 9.69 mmol), NH4Cl (1.04 g, 19.38 mmol), HATU (5.5 g, 14.5 mmol), and DIPEA (5.2 mL, 29.1 mmol) in DCM (50 mL) was stirred for 3 h at rt. Water was added and the mixture was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (3:1) to give methyl 2-bromo-4-carbamoylbenzoate (1.3 g; yield 52%) as a white solid. MS: m/z=257.9 (M+1, ESI+).

Workup

  1. extractionthe mixture was extracted with DCM
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel
  7. washeluted with PE-EA (3:1)

Sources & evidence

ORD record
ord-4d132f5ef33c441382eb69ab88d7f62a
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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