Triisopropyl borate → 3-Fluoro-4-methoxyphenylboronic acid

HRID 1830639Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([F:10])[CH:3]=1.C([Li])CCC.[B:16](OC(C)C)([O:21]C(C)C)[O:17]C(C)C>>[F:10][C:4]1[CH:3]=[C:2]([B:16]([OH:21])[OH:17])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

Participants

Reactant 3

HCID 21531Triisopropyl borate

HCID 753784-Bromo-2-fluoroanisole

HCID 178418339Butyllithium

Product 1

HCID 27821943-Fluoro-4-methoxyphenylboronic acid

Procedure

The title compound was prepared by reacting 4-bromo-2-fluoroanisole (10 g, 0.049 mol) with n-butyl lithium (23.4 mL of 2.5 M solution in hexane, 0.059 mol) followed by triisopropyl borate (45.2 mL, 36.9 g, 0.196 mol) according to method F to yield 7.1 g (85.2%) of a white solid: MS (ESI) m/z 169 (M−H)−: 1H NMR (DMSO-d6): δ 3.84 (3H, s), 7.10–7.16 (1H, m), 7.51–7.60 (2H, m).

Sources & evidence

ORD record: ord-62036d36db1f425bab4572e3c8deb253
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

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