Hydrochloric Acid → 3-Bromo-5-methanesulfonylbenzoic acid

HRID 1845219Notes

Reaction equation

HRID 1845219 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:11]=1)[C:5]([O:7]C)=[O:6].[OH-].[Li+].O1CCCC1.Cl>O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:11]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 22101072Methyl 3-bromo-5-methanesulfonylbenzoate

Product 1

HCID 543046163-Bromo-5-methanesulfonylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of methyl 3-bromo-5-(methylsulfonyl)benzoate (0.65 g, 2.2 mmol), lithium hydroxide (0.26 g, 11 mmol), tetrahydrofuran (25 mL) and water (5 mL) was stirred at room temperature for 3 h. Water (50 mL) was added and the mixture was acidified with 1N aq. HCl to pH 2-3 and extracted with EtOAc (100 mL). The organic layer was separated, washed with brine, dried (Na2SO4), and concentrated to yield a white solid. LC-MS: 278.6 [M−1]−; 1H NMR (400 MHz, CDCl3): 8.59 (m, 1H), 8.50 (m, 1H), 8.33 (m, 1H), 3.13 (s, 3H).

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto yield a white solid

Sources & evidence

ORD record
ord-6f6a00b3ba3c4b3b987f218b817a573a
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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