Water → Methyl 4-bromo-2-isopropoxycarbonylaminobenzoate

HRID 2353871Notes

Reaction equation

HRID 2353871 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[NH2:8][C:9]1[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].N1C=CC=CC=1.O>ClCCl>[Br:19][C:17]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([NH:8][C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3])[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 17871390Methyl 2-Amino-4-bromobenzoate

Product 1

HCID 68680673Methyl 4-bromo-2-isopropoxycarbonylaminobenzoateYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add isopropyl chloroformate (104 mL, 104 mmol, 1.0 M in toluene) dropwise to a solution of methyl 2-amino-4-bromobenzoate (14.5 g, 63.0 mmol) and pyridine (10.3 mL, 126.0 mmol) in dichloromethane (210 mL) at room temperature under nitrogen and stir for 5.5 h. Pour the reaction into water (500 mL) and separate the layers. Extract the aqueous layer with dichloromethane (2×100 mL) and combine the organic extracts and wash with 2 N HCl, saturated sodium bicarbonate and brine (100 mL each), then dry over sodium sulfate, filter and remove the solvent under reduced pressure to afford the title compound as a pale orange solid (19.2 g, 96%)

Workup

  1. additionPour
  2. customseparate the layers
  3. extractionExtract the aqueous layer with dichloromethane (2×100 mL)
  4. washwash with 2 N HCl, saturated sodium bicarbonate and brine (100 mL each)
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-af8594ca17a2427086fc588acec78210
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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