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

HRID 10277Notes

Reaction equation

HRID 10277 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-fe4ad7640e624dbfaf995746fd968f26
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

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