Hydrochloric Acid → (2,2-Difluoro-1,3-dioxaindan-5-yl)boronic acid

HRID 1348906Notes

Reaction equation

HRID 1348906 reaction equation
C([Li])(C)(C)C.CCCCC.Br[C:12]1[CH:22]=[CH:21][C:15]2[O:16][C:17]([F:20])([F:19])[O:18][C:14]=2[CH:13]=1.C([O:26][B:27](OC(C)C)[O:28]C(C)C)(C)C.[OH-].[Na+].Cl>C(OCC)C>[F:19][C:17]1([F:20])[O:16][C:15]2[CH:21]=[CH:22][C:12]([B:27]([OH:28])[OH:26])=[CH:13][C:14]=2[O:18]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8003PentaneHCID 14798Sodium HydroxideHCID 21531Triisopropyl borateHCID 27362715-Bromo-2,2-difluoro-1,3-benzodioxoleHCID 178418306HCID 178418306, compound

Product 1

HCID 17750030(2,2-Difluoro-1,3-dioxaindan-5-yl)boronic acidYield 95.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.5M tert-butyllithium in pentane (130 mL, 195 mmol) in diethyl ether (500 mL) at −78° C. was treated with 5-bromo-2,2-difluoro-1,3-benzodioxole (18 g, 76 mmol) in diethyl ether (80 mL), stirred for 1 hour, treated with triisopropylborate (37 mL, 160 mmol), warmed to room temperature over 1 hour, poured into 4M NaOH (700 mL), stirred for 15 minutes, cooled, adjusted to pH 1 with concentrated HCl, and extracted with ethyl acetate. The extract was washed with brine, dried (Na2SO4), filtered, and concentrated to provide 14.7 g (95%) of the desired product. 1H NMR (DMSO-d6) δ 7.75 (m, 1H), 7.66 (m, 1H), 7.51 (m, 1H), 7.39 (m, 1H), 7.30 (m, 1H).

Workup

  1. stirringstirred for 15 minutes
  2. temperaturecooled
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-568a6ec2f4a34f399ff6568dd02900ff
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

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