Methanol → 3-Bromo-5-(pyrrolidine-1-carbonyl)benzoic acid

HRID 1845179Notes

Reaction equation

HRID 1845179 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])[CH:11]=1)[C:5]([O:7]C)=[O:6].[OH-].[Li+].CO>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])[CH:11]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 58188186Methyl 3-bromo-5-(pyrrolidine-1-carbonyl)benzoate

Product 1

HCID 581881193-Bromo-5-(pyrrolidine-1-carbonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a round-bottom flask were charged methyl 3-bromo-5-(pyrrolidine-1-carbonyl)benzoate (0.86 g, 2.5 mmol), lithium hydroxide (0.071 g, 3.0 mmol), methanol (5 mL) and water (5 mL). The mixture was stirred at room temperature for 2 h. Methanol was removed under reduced pressure. The aqueous layer was acidfied to pH=1 with 1N aq. HCl, and then extracted with CH2Cl2. The separated organic phase was dried over Na2SO4, filtered, and concentrated to dryness to afford the desired product as a white solid. 1H NMR (400 MHz, DMSO-d6): 13.54 (br, 1H), 8.09 (t, J=1.6 Hz, 1H), 7.98 (t, J=1.5 Hz, 1H), 7.94 (t, J=1.8 Hz, 1H), 3.47 (t, J=6.7 Hz, 2H), 3.37 (t, J=6.5 Hz, 2H), 1.90-1.80 (m, 4H).

Workup

  1. customMethanol was removed under reduced pressure
  2. extractionextracted with CH2Cl2
  3. dry with materialThe separated organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ef1539bcbbf74979871eedde0b4b4182
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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