Sodium Hydroxide → HCID 66801910, compound

HRID 2366306Notes

Reaction equation

HRID 2366306 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 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 2-chloro-6-fluoroterephthalate (6.19 g, 25.1 mmol) in tetrahydrofuran (75 mL) was added a solution of 1 N NaOH (27.6 mmol, 27.6 mL). The reaction mixture was stirred at room temperature for 30 min. After the volatiles were removed under reduced pressure, water (30 mL) was added. The aqueous solution was acidified with 1 N HCl to pH 3.0. A white solid precipitated and was collected by filtration, washed with water and diethyl ether, dried in high vacuum to afford the title compound as a white solid (5.54 g, 95% yield). 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+) 233.0 [M+H]+.

Workup

  1. customAfter the volatiles were removed under reduced pressure, water (30 mL)
  2. additionwas added
  3. customA white solid precipitated
  4. filtrationwas collected by filtration
  5. washwashed with water and diethyl ether
  6. customdried in high vacuum

Sources & evidence

ORD record
ord-9d3f6550362d4bc788169047922c66e8
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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