Hydrochloric Acid → 4-fluoro-3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol

HRID 1037055Notes

Reaction equation

HRID 1037055 reaction equation
[F:1][C:2]1[C:3]([C:18]([O:21]COC)([CH3:20])[CH3:19])=[C:4]([B:9]2[O:13]C(C)(C)C(C)(C)O2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl>>[F:1][C:2]1[C:3]2[C:18]([CH3:19])([CH3:20])[O:21][B:9]([OH:13])[C:4]=2[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 866855012-(3-Fluoro-2-(2-(methoxymethoxy)propan-2-yl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 866855004-fluoro-3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-olYield 52.5%

Procedure

The crude 2-(3-fluoro-2-(2-(methoxymethoxy)propan-2-yl)-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was mixed with 25 ml of 6N HCl and the reaction mixture was stirred at rt overnight. The reaction was monitored by LC-MS. The reaction solution was extracted with EtOAc, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (5:1 to 2:1) to give 4-fluoro-3,3,6-trimethylbenzo[c][1,2]oxaborol-1(3H)-ol (3.5 g, 52.5% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.17 (s, 1H), 7.30 (s, 1H), 7.08 (d, J=11.2 Hz, 1H), 2.34 (s, 3H), 1.49 (s, 6H) ppm.

Workup

  1. extractionThe reaction solution was extracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel
  6. washeluted with PE-EA (5:1 to 2:1)

Sources & evidence

ORD record
ord-2fa12c34198c45cb905ace63b7f1b3d6
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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