Trimethyl borate → Boronic acid, B-[3-(hydroxymethyl)-2-methylphenyl]-

HRID 2215985Notes

Reaction equation

HRID 2215985 reaction equation
[CH2:1]([Li])CCC.I[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1C)[CH2:10][OH:11].C[O:17][B:18](OC)[O:19]C>>[OH:11][CH2:10][C:9]1[C:8]([CH3:1])=[C:7]([B:18]([OH:19])[OH:17])[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 8470Trimethyl borateHCID 51667983-Iodo-4-methylbenzyl alcoholHCID 178418339Butyllithium

Product 1

HCID 21886047Boronic acid, B-[3-(hydroxymethyl)-2-methylphenyl]-Yield 27.1%

Procedure

Butyllithium (2.5 M, 4 mL, 10 mmol), 3-iodo-4-methyl-benzyl alcohol (1 g, 4 mmol), and trimethylborate (6 mL, 53 mmol) were reacted as in Example 5: step b. Aqueous workup and purification by SiO2 flash chromatography (40–50% EtOAc in hexanes) yielded the title compound (180 mg, 27%). The title compound exists as a mixture of boronic acids and anhydrides in CDCl3, therefore the reported NMR signals represent pairs or groups of related signals. 1H-NMR (CDCl3): δ 7.06–7.30 (m, 3H), 4.56 (s, 3H), 4.16 (br s, 1H), 2.32 (s, 3H).

Workup

  1. customAqueous workup and purification by SiO2 flash chromatography (40–50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6ae13df908f94e1c807fd863985282c5
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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