Trimethyl borate → 4-(2-(Tert-butyldimethylsilyloxy)ethyl)-3,5-dimethylphenylboronic acid

HRID 735625Notes

Reaction equation

HRID 735625 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([B:17]([OH:19])[OH:18])=[CH:13][C:12]=1[CH2:20]C)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:23]1C=C(C)C(CCO[Si](C(C)(C)C)(C)C)=C(C)C=1.COB(OC)OC>>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[C:12]([CH3:20])=[CH:13][C:14]([B:17]([OH:18])[OH:19])=[CH:15][C:16]=1[CH3:23])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 8470Trimethyl borateHCID 57842569(4-Bromo-2,6-dimethylphenethoxy)(tert-butyl)dimethylsilaneHCID 578426084-(2-(Tert-butyldimethylsilyloxy)ethyl)-3-ethylphenylboronic acid

Product 1

HCID 578425504-(2-(Tert-butyldimethylsilyloxy)ethyl)-3,5-dimethylphenylboronic acidYield 45%

Procedure

Using a procedure analogous to that used to prepare 46B, 50A (3.58 g, 10.5 mmol) was reacted trimethylborate to afford 50B (1.45 g, 45%) as a white solid. 1H NMR (400 MHz, MeOD) δ ppm −0.03 (s, 6 H) 0.85 (s, 9 H) 2.33 (s, 6 H) 2.92 (t, J=7.15 Hz, 2 H) 3.75 (t, J=7.42 Hz, 2 H) 7.20 (s, 2 H).

Sources & evidence

ORD record
ord-d83cd09ec6de4f8cab63921bd7232b0a
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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