Lithium Hydroxide → 4'-Bromo-4-(dimethylamino)biphenyl-2-carboxylic acid

HRID 1043435Notes

Reaction equation

HRID 1043435 reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:19]([O:21]C)=[O:20])=[CH:12][C:13]([N:16]([CH3:18])[CH3:17])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1>C1COCC1.CO.Cl>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]([C:19]([OH:21])=[O:20])=[CH:12][C:13]([N:16]([CH3:17])[CH3:18])=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 59266543Methyl 4'-bromo-4-(dimethylamino)biphenyl-2-carboxylate

Product 1

HCID 592665644'-Bromo-4-(dimethylamino)biphenyl-2-carboxylic acidYield 74%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2M Lithium hydroxide (8.5 mL, 17.0 mmol) was added to a solution of methyl 4′-bromo-4-(dimethylamino)biphenyl-2-carboxylate (1.9 g, 5.69 mmol) in THF (20 mL) and methanol (20 mL) and stirred at r.t. for 18 hrs. The reaction was then diluted with 1M HCl and extracted with EtOAc. The organic layer was washed with water then brine, dried over MgSO4, filtered and then evaporated to give 4′-bromo-4-(dimethylamino)biphenyl-2-carboxylic acid (1.34 g, 4.19 mmol, 74% yield) as a white solid. LCMS: rt=1.54 min. [M+H]+=319 and 321; Phenomenex-Luna C-18 (5μ) (3.0×50 mm); Solvent. A=10% acetonitrile—90% water—0.1% TFA, Solvent B=90% acetonitrile—10% water—0.1% TFA; gradient 0% to 100% solvent B over 2 min. and then hold for 1 min.; 4 mL/min; inj. vol.=5 uL; wavelength=220.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9c44dc78301a460d9f0b5a2f34e4c64e
Source dataset
uspto-grants-2013_10
Patent number
US08563505B2

Reaction notes

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