Tetrahydrofuran → HCID 22637025, compound

HRID 459841

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4](Cl)[CH:3]=1.C([Li])CCC.CCCCCC.[B:22]([O:27]C)([O:25]C)[O:23]C.C1C[O:32][CH2:31]C1>>[CH3:31][O:32][C:4]1[CH:3]=[C:2]([O:27][B:22]([OH:23])[OH:25])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 8470Trimethyl borate

HCID 30165374-Bromo-2-chloroanisole

HCID 178418244HCID 178418244, compound

Product 1

HCID 22637025HCID 22637025, compound

Procedure

To a THF solution of 4-bromo-2-chloroanisole was added an n-butyllithium/n-hexane solution at −78° C., followed by 30 minutes of stirring. Then, trimethyl borate was added and the whole was warmed to room temperature, followed by 30 minutes of stirring. Using the residue obtained by evaporation of the solvent instead of 3,4-dimethoxyphenylboric acid, an objective compound was obtained in a similar manner to Reference Example 1.

Workup

waitfollowed by 30 minutes
stirringof stirring

Sources & evidence

ORD record: ord-1115ae46fc4c4112a137d8b25c599060
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196080B2

Linked notes

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