Hydrochloric Acid → HCID 86685087, compound

HRID 532224Notes

Reaction equation

HRID 532224 reaction equation
C(OCOC([C:9]1[C:14]([F:15])=[C:13]([CH3:16])[CH:12]=[CH:11][C:10]=1[B:17]1[O:21][C:20]([CH3:23])([CH3:22])C(C)(C)[O:18]1)(C)C)C.Cl>C1COCC1>[F:15][C:14]1[C:9]2[C:20]([CH3:22])([CH3:23])[O:21][B:17]([OH:18])[C:10]=2[CH:11]=[CH:12][C:13]=1[CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86685088HCID 86685088, compound

Product 1

HCID 86685087HCID 86685087, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude compound 2-(2-(2-(ethoxymethoxy)propan-2-yl)-3-fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.17 g, 14.7 mmol) in THF (147 mL) was added 6 N HCl (147 mL). The reaction mixture was stirred at room temperature overnight, and the resulting mixture was extracted three times with ethyl acetate. The combined extracts were washed with water and brine, dried over with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with PE-EA (10:1) to give 4-fluoro-3,3,5-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (1.52 g, 53.8% yield over 2 steps) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.339 (d, J=7.5 Hz, 1H), 7.200 (t, J=6.5 Hz, 1H), 5.652 (s, 1H), 2.330 (s, 3H), 1.642 (s, 6H) ppm.

Workup

  1. extractionthe resulting mixture was extracted three times with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluted with PE-EA (10:1)

Sources & evidence

ORD record
ord-c1196331b0254edc8cabe5c30f78532d
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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