Triethylamine → Methyl 5-bromo-2-(2-phenoxyacetamido)benzoate

HRID 520839Notes

Reaction equation

HRID 520839 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[O:13]([CH2:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>ClCCl>[Br:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][C:21](=[O:22])[CH2:20][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 736224Methyl 2-amino-5-bromobenzoate

Product 1

HCID 7765744Methyl 5-bromo-2-(2-phenoxyacetamido)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of commercially available methyl 2-amino-5-bromobenzoate (10.0 g, 43.5 mmol) in dichloromethane (100 mL) was added 2-phenoxyacetyl chloride (6.60 mL, 47.8 mmol). The white suspension formed was cooled to 0° C. and treated with triethylamine (13.3 mL, 95.6 mmol) dropwise. The resulting solution was stirred at room temperature for 0.5 hours. The mixture was diluted with CH2Cl2 and was washed with water and saturated aqueous NH4Cl solution. The organic phase was dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 7% EtOAc-heptane), to afford the title compound.

Workup

  1. customThe white suspension formed
  2. washwas washed with water and saturated aqueous NH4Cl solution
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (silica gel, 7% EtOAc-heptane)

Sources & evidence

ORD record
ord-2a6ef8f294384856a98aa5dbd7fdd63e
Source dataset
uspto-grants-2016_05
Patent number
US09328095B2

Reaction notes

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