Sodium Hydroxide → HCID 58083439, compound

HRID 2404336Notes

Reaction equation

HRID 2404336 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([O:12]C)=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:23])([F:22])[F:21]>CO>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:21])([F:22])[F:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66718347Methyl 2-chloro-2'-(trifluoromethyl)biphenyl-4-carboxylate

Product 1

HCID 58083439HCID 58083439, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 5N aqueous solution of NaOH (4 mL, 20 mmol) was added into a solution of methyl 2-chloro-2′-(trifluoromethyl)biphenyl-4-carboxylate (1.07 g, 3.40 mmol) in MeOH (16 mL) and stirred at RT for 30 minutes. The reaction mixture was concentrated under vacuum. The residue was taken up with EtOAc and washed with a 1N aqueous solution of HCl (3×) and brine, and then dried (MgSO4) and concentrated under vacuum to give the title compound as a white powder (950 mg, 93%). HPLC (Method A) Rt 4.9 min (Purity: 99.4%). LC/MS (Method B): 299.1 (M−H)−. 1H NMR (DMSO-d6, 300 MHz) δ 13.48 (s, 1H), 8.03 (d, J=1.6 Hz, 1H), 7.94 (dd, J=7.9, 1.6 Hz, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.78 (m, 1H), 7.69 (m, 1H), 7.49 (d, J=7.9 Hz, 1H), 7.41 (d, J=7.4 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. washwashed with a 1N aqueous solution of HCl (3×) and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-673507b35e6b4c57abb9b3aa47c9258e
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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