Hydrochloric Acid → HCID 86672791, compound

HRID 1755085Notes

Reaction equation

HRID 1755085 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([O:14][CH2:15][C:16]([F:21])([F:20])[CH:17]([F:19])[F:18])[CH:8]=1.[B:22](OC(C)C)([O:27]C(C)C)[O:23]C(C)C.Cl>O1CCCC1>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([B:22]([OH:27])[OH:23])=[CH:8][C:9]=1[O:14][CH2:15][C:16]([F:21])([F:20])[CH:17]([F:19])[F:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 86672792HCID 86672792, compoundHCID 178418339Butyllithium

Product 1

HCID 86672791HCID 86672791, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.5 M solution of n-butyllithium in tetrahydrofuran (0.99 mL) was added to a solution of 4-bromo-1-chloro-2-(2,2,3,3-tetrafluoro-propoxy)-benzene (434 mg, 1.35 mmol) and triisopropyl borate (382 mg, 2.03 mmol) in anhydrous tetrahydrofuran (2.0 mL) at −78° C., and the mixture was stirred for 10 minutes. The reaction mixture was warmed to room temperature and stirred for 30 minutes. 6 N aqueous hydrochloric acid was then added to the reaction mixture, and the reaction was terminated, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was treated with a mixed solution of dichloromethane and hexane to give 4-chloro-3-(2,2,3,3-tetrafluoro-propoxy)-phenylboronic acid as a white solid (246 mg, 64%).

Workup

  1. stirringstirred for 30 minutes
  2. customthe reaction was terminated
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue was treated with a mixed solution of dichloromethane and hexane

Sources & evidence

ORD record
ord-31f93d5b1fce494fa40a88fe66f7052a
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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