Lithium Hydroxide → HCID 86708463, compound

HRID 921616Notes

Reaction equation

HRID 921616 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:11]=1[Cl:12])[C:5]([O:7]C)=[O:6].[Li+].[OH-]>C1COCC1.CO.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:11]=1[Cl:12])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86708461HCID 86708461, compound2×

Product 1

HCID 86708463HCID 86708463, compoundYield 98.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(I5A): A stirred solution of methyl 3-bromo-5-((tert-butoxycarbonyl)amino)-4-chlorobenzoate (1 g, 2.74 mmol, Intermediate 4) in THF (15 mL), MeOH (3.75 mL) and water (3.75 mL) was treated with LiOH (0.263 g, 10.97 mmol). The reaction was stirred at rt for 2 h. The reaction mixture was concentrated and the white residue was suspended in water, then neutralized with AcOH to pH ˜6-7. The suspension was stirred for 30 min, then the white solid was collected by filtration and dried in air to yield 3-bromo-5-((tert-butoxycarbonyl)amino)-4-chlorobenzoic acid (0.95 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. stirringThe suspension was stirred for 30 min
  3. filtrationthe white solid was collected by filtration
  4. customdried in air

Sources & evidence

ORD record
ord-9dc7b416a5c74ddb98c9afce27bfc4f1
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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