Hydrochloric Acid → 3-METHYLTHIOPHENE-2-BORONIC ACID

HRID 1913359Notes

Reaction equation

Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH3:7].[Li]CCCC.[B:13](OC(C)C)([O:18]C(C)C)[O:14]C(C)C.Cl>>[B:13]([OH:18])([OH:14])[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH3:7]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 21531Triisopropyl borate

HCID 843142-Bromo-3-methylthiophene

HCID 178418339Butyllithium

Product 1

HCID 32764373-METHYLTHIOPHENE-2-BORONIC ACIDYield 93%

Procedure

2-Bromo-3-methylthiophene was treated with n-BuLi (1.6 M in hexanes, 38.8 mL, 62.1 mmol), triisopropyl borate (15.1 mL, 65.4 mmol) and HCl(aq) (2.7 N, 52.5 mL) as for 1 to give the title compound 5 (7.2 g, 93% yield) as a brown solid: 1H NMR (CD3OD) δ 7.27 (d, J=5.5 Hz, 1H), 6.80 (d, J=5.5 Hz, 1H), 2.16 (s, 3H). This material was used directly in Suzuki cross coupling reactions.

Sources & evidence

ORD record: ord-89d1fee75ef34846ae74ade8807e891a
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609708B2

Reaction notes

Loading…