Triisopropyl borate → 3-Benzyloxy-phenylboronic acid

HRID 1600976Notes

Reaction equation

HRID 1600976 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[B:21](OC(C)C)([O:26]C(C)C)[O:22]C(C)C>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([B:21]([OH:26])[OH:22])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 27566381-(Benzyloxy)-3-bromobenzeneHCID 178418339Butyllithium

Product 1

HCID 27343133-Benzyloxy-phenylboronic acidYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to the method described in Example 51b) from 3-(benzyloxy)bromobenzene (2.16 g, Example 93a), n-butyllithium (2.5 M in hexanes, 3.6 ml) and triisopropyl borate (3.4 g), in tetrahydrofuran (2×10 ml). After work up the residue was purified by column chromatography over silica eluting with ethyl acetate:hexane:acetic acid (20:79.5:0.5) then methanol to give the sub-title compound as a white solid (1.04 g). This was used without analysis.

Workup

  1. customPrepared
  2. customAfter work up the residue was purified by column chromatography over silica eluting with ethyl acetate:hexane:acetic acid (20:79.5:0.5)

Sources & evidence

ORD record
ord-7812296945b740c5a1ec0fbcf234883b
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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