Hydrochloric Acid → 4-Ethoxycarbonylphenylboronic acid

HRID 2356058Notes

Reaction equation

HRID 2356058 reaction equation
[OH:1][B:2]([OH:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.Cl.[CH2:14](O)[CH3:15]>O1CCOCC1>[CH2:14]([O:8][C:7]([C:6]1[CH:10]=[CH:11][C:3]([B:2]([OH:12])[OH:1])=[CH:4][CH:5]=1)=[O:9])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 27343504-Ethoxycarbonylphenylboronic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 4-(dihydroxyboryl)benzoic acid (5.0 g, 30.13 mmol) in ethanol (16.0 mL) was treated with 4N HCl in dioxane (34.0 mL), heated to reflux, stirred for 1.5 hours, and concentrated. The concentrate was partitioned between water (150.0 mL) and diethyl ether (100.0 mL) and the aqueous layer was extracted with diethyl ether (2×100 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated to provide the desired product. MS (APCI) m/e 194 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.07 (m, 2H), 7.81 (m, 2H), 4.41 (q, 2H), 1.41 (t, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. concentrationconcentrated
  4. customThe concentrate was partitioned between water (150.0 mL) and diethyl ether (100.0 mL)
  5. extractionthe aqueous layer was extracted with diethyl ether (2×100 mL)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-664d983cb0fa4b209a112c245be3fc05
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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