Hydrochloric Acid → (5-Cyano-1-benzofuran-2-yl)boronic acid

HRID 1897578Notes

Reaction equation

HRID 1897578 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Li]CCCC.[B:17](OC)([O:20]C)[O:18]C.Cl>C1COCC1>[C:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][C:2]([B:17]([OH:20])[OH:18])=[CH:3][C:4]=2[CH:9]=1)#[N:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 27951841-Benzofuran-5-carbonitrileHCID 178418339Butyllithium

Product 1

HCID 66787891(5-Cyano-1-benzofuran-2-yl)boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To benzofuran-5-carbonitrile (500 mg, 3.49 mmol) in THF (9.98 mL) at −78° C. was added n-BuLi 1.6M in hexanes (2.401 mL, 3.84 mmol) dropwise. The mixture was stirred for 30 min at this temperature, and then trimethyl borate (0.858 mL, 7.68 mmol) was added dropwise. The mixture was stirred for 20 min, and then HCl (2M, 11.52 mL, 23.05 mmol) was added. The bath was removed, and then stirred for 30 min. To the mixture was added more water and extracted with EtOAc three times, dried over magnesium sulfate, filtered, concentrated. crude 7a (623 mg, 87%) was then dried and used as is for next step.

Workup

  1. stirringThe mixture was stirred for 20 min
  2. customThe bath was removed
  3. stirringstirred for 30 min
  4. additionTo the mixture was added more water
  5. extractionextracted with EtOAc three times
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dry with materialcrude 7a (623 mg, 87%) was then dried

Sources & evidence

ORD record
ord-b2dcab8129ff4e2abe6e4b07ba6ac11c
Source dataset
uspto-grants-2013_08
Patent number
US08519134B2

Reaction notes

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