Hydrochloric Acid → 3-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid

HRID 729366Notes

Reaction equation

HRID 729366 reaction equation
[F:1][C:2]1[C:10]([CH:11]=O)=[C:9]([F:13])[C:8]([F:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N(CC)CC)C.Cl.[CH2:23]([O:30][NH2:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>[Cl-].[Na+].O.O1CCCC1>[CH2:23]([O:30][N:31]=[CH:11][C:10]1[C:2]([F:1])=[C:3]([CH:7]=[C:8]([F:14])[C:9]=1[F:13])[C:4]([OH:6])=[O:5])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 102312Benzyloxyamine hydrochlorideHCID 219793442,4,5-Trifluoro-3-formylbenzoic acid

Product 1

HCID 738573153-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2,4,5-Trifluoro-3-formylbenzoic acid (Horiuchi N., Yonezawa T., Chiba K., Yoshida H., PCT Int. Appl. [1999] WO 97-JP2918), (5.70 g, 27.9 mmol), triethylamine (11 mL, 78.9 mmol), O-benzylhydroxylamine hydrochloride (4.47 g, 28.0 mmol) and anhydrous tetrahydrofuran (150 mL) are stirred at room temperature for 50 hours. The mixture is poured into brine and the pH adjusted to 5.5-6.0 using 1.0 M hydrochloric acid. The mixture is extracted with ethyl acetate. The organic phase is dried over Na2SO4, filtered, and concentrated in vacuo to provide 3-(benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid (8.63 g), which is used without further purification. 1H NMR (200 MHz, CDCl3): δ 9.82-9.18 (bs, 1H), 8.24 (s, 1H), 7.94-7.68 (m, 1H), 7.55-7.23 (m, 5H), 5.23 (d, 2H). MS (EI, M−1) m/z 308.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60ad8bd6eb3f4c44be2832308b8fb9d9
Source dataset
uspto-grants-2009_09
Patent number
US07582627B2

Reaction notes

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