Lithium Hydroxide → 3-Bromo-2-(((tert-butoxycarbonyl)amino)methyl)benzoic acid

HRID 1826994Notes

Reaction equation

HRID 1826994 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[Br:17])[C:9]1=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:19].[Li+]>O1CCCC1.C(OCC)C>[C:1]([O:5][C:6]([NH:8][CH2:16][C:15]1[C:14]([Br:17])=[CH:13][CH:12]=[CH:11][C:10]=1[C:9]([OH:18])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86593478Tert-butyl 4-bromo-1-oxoisoindoline-2-carboxylate

Product 1

HCID 221368283-Bromo-2-(((tert-butoxycarbonyl)amino)methyl)benzoic acidYield 86.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-bromo-1-oxo-1,3-dihydro-isoindole-2-carboxylic acid tert butyl ester (0.206 g, 0.66 mmol) in tetrahydrofuran (10 ml) was added dropwise a solution of aq. lithium hydroxide (1M, 2 ml, 1.98 mmol) and the mixture stirred at room temperature under nitrogen for 18 hours. The mixture was diluted with diethyl ether (30 ml) and washed with 1M HCl (10 ml). The aqueous layer was extracted with diethyl ether (2×20 ml) and the combined organics dried over magnesium sulfate, filtered and the solvent removed by evaporation under reduced pressure to give the title compound (0.188 g, 86%) as a white waxy solid.

Workup

  1. washwashed with 1M HCl (10 ml)
  2. extractionThe aqueous layer was extracted with diethyl ether (2×20 ml)
  3. dry with materialthe combined organics dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b3dc4b68f1324c3fb040b4a8f77f7796
Source dataset
uspto-grants-2006_05
Patent number
US07053122B2

Reaction notes

Loading…