Triisopropyl borate → (6-Methyl-1-benzothiophen-2-yl)boronic acid

HRID 2353354Notes

Reaction equation

HRID 2353354 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.[Li]CCCC.[B:16](OC(C)C)([O:21]C(C)C)[O:17]C(C)C>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([B:16]([OH:21])[OH:17])[S:7][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 357906-Methyl-1-benzothiopheneHCID 178418339Butyllithium

Product 1

HCID 53398048(6-Methyl-1-benzothiophen-2-yl)boronic acidYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-methyl-benzo[b]thiophene (0.16 g, 0.001 mol) in 10 mL of anhydrous THF at −60° C. is added n-BuLi (0.8 mL, 0.0012 mol) dropwise via syringe. After stirring for 30 minutes triisopropyl borate (0.3 mL, 0.0012 mol) is added dropwise. The reaction mixture is allowed to warm to 0° C. and then partitioned between 1.0N HCl and EtOAc. The organic layer is separated, dried, filtered and concentrated to produce a white solid that is triturated from ether/hexane. Filtration provides 0.17 g of 6-Methyl-benzo[b]thiophene-2-boronic acid as white solid. MS m/z 193 [M+1]+.

Workup

  1. additionis added dropwise
  2. custompartitioned between 1.0N HCl and EtOAc
  3. customThe organic layer is separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto produce a white solid
  8. customthat is triturated from ether/hexane
  9. filtrationFiltration

Sources & evidence

ORD record
ord-6eefdb3f6afe47edbc1442c9f0559497
Source dataset
uspto-grants-2010_07
Patent number
US07750021B2

Reaction notes

Loading…