HCID 21877338, compound → HCID 21877382, compound

HRID 724405Notes

Reaction equation

HRID 724405 reaction equation
Br[C:2]1[C:16]([CH3:17])=[CH:15][C:5]([O:6][CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([Cl:18])[CH:3]=1.COC1C(OCOCC[Si](C)(C)C)=CC(C)=C([B:27]([OH:29])[OH:28])C=1>>[Cl:18][C:4]1[C:5]([O:6][CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:15][C:16]([CH3:17])=[C:2]([B:27]([OH:29])[OH:28])[CH:3]=1

Participants

3

Reactant 2

HCID 21877338HCID 21877338, compoundHCID 21877347HCID 21877347, compound

Product 1

HCID 21877382HCID 21877382, compoundYield 54%

Procedure

5-Chloro-2-methyl-4-[2-(trimethyl-silanyl)-ethoxymethoxy]-phenyl-boronic acid was prepared in 54% yield from [2-(4-bromo-2-chloro-5-methyl-phenoxymethoxy)-ethyl]-trimethyl-silane according to the procedure for 5-methoxy-2-methyl-4-[2-(trimethyl-silanyl)-ethoxymethoxy]-phenyl-boronic acid. 1H NMR (300 MHz, CDCl3) δ 8.11 (s, 1 H), 7.09 (s, 1 H), 5.37 (s, 2 H), 3.84 (t, 2 H, J=8.4 Hz), 2.76 (s, 3 H), 0.98 (t, 2 H, J=8.4 Hz), 0.01 (s, 9 H). Anal. (C13H22BClO4Si—H2O) C, H. Calculated: C, 52.28; H, 6.75. Found: C, 51.98; H, 6.84.

Sources & evidence

ORD record
ord-cb84fec66f9640a3aad4da947bd61b9b
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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