Triisopropyl borate → 3-Fluoro-4-methoxyphenylboronic acid

HRID 1180337Notes

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 moles) with n-butyl lithium (23.4 mL of 2.5 M solution in hexane, 0.059 moles) followed by triisopropyl borate (45.2 mL, 36.9 g, 0.196 moles) according to Method A to yield 7.1 g (85.2%) of a white solid: MS (ESI) m/z 169 (M−H)−.

Sources & evidence

ORD record: ord-bc4e86bc7a794eb5ae2ce36406c17597
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279600B2

Reaction notes

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