Sodium Hydroxide → HCID 66801910, compound

HRID 449926Notes

Reaction equation

HRID 449926 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([O:14]C)=[O:13])[CH:9]=[C:8]([F:16])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]([CH:9]=[C:8]([F:16])[C:3]=1[C:4]([O:6][CH3:7])=[O:5])[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66801766HCID 66801766, compound

Product 1

HCID 66801910HCID 66801910, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 2-chloro-6-fluoroterephthalate (2.784 g, 11.3 mmoles) in tetrahydrofuran (20 mL) was added a solution of 1 N NaOH (12.4 mmol, 12.4 mL). The reaction mixture was stirred at room temperature for 30 min. The reaction was concentrated under reduced pressure and the residue was suspended in water (10 mL). The aqueous solution was acidified to pH 3 with 1 N HCl. The resulting white precipitate was collected by filtration, washed with water and ether, dried in high vacuum to afford 3-chloro-5-fluoro-4-(methoxycarbonyl)benzoic acid as a white solid (2.52 g, yield: 96%). 1H NMR (400 MHz, CDCl3) δ 7.96 (s, 1H), 7.76 (dd, J=8.8, 1.3 Hz, 1H), 4.01 (s, 3H). LCMS (APCI+) [M+H]+233.0.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. filtrationThe resulting white precipitate was collected by filtration
  3. washwashed with water and ether
  4. customdried in high vacuum

Sources & evidence

ORD record
ord-588e676ff8d74d5e9bae935201a49f17
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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