5-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 2-trimethylsilanyl-ethyl ester → 2-(3-tert-Butoxycarbonyl-propoxy)-4-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid-2-trimethylsilanyl-ethyl ester

HRID 448928Notes

Reaction equation

HRID 448928 reaction equation
C[Si](C)(C)CCOC(=O)C1C=CC=CC=1[B:13]1[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]1.[CH3:25][Si:26]([CH3:52])([CH3:51])[CH2:27][CH2:28][O:29][C:30](=[O:50])[C:31]1[CH:36]=[C:35](Br)[C:34]([Cl:38])=[CH:33][C:32]=1[O:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]>>[CH3:25][Si:26]([CH3:52])([CH3:51])[CH2:27][CH2:28][O:29][C:30](=[O:50])[C:31]1[CH:36]=[C:35]([B:13]2[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]2)[C:34]([Cl:38])=[CH:33][C:32]=1[O:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]

Participants

3

Reactant 2

HCID 686027085-Bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 2-trimethylsilanyl-ethyl esterHCID 866425774,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl-benzoic acid-2-trimethylsilanyl-ethyl ester

Product 1

HCID 686044912-(3-tert-Butoxycarbonyl-propoxy)-4-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid-2-trimethylsilanyl-ethyl ester

Procedure

2-(3-tert-Butoxycarbonyl-propoxy)-4-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl-benzoic acid-2-trimethylsilanyl-ethyl ester (2.7 g) was similarly prepared according to Step 2D from 5-bromo-2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-benzoic acid 2-trimethylsilanyl-ethyl ester (3.2 g). MS ion (APCl): 513.2, 459.1; tR=3.62 min. (method 1)

Sources & evidence

ORD record
ord-4c7a18e242c14bb9be9579e7443ce1c4
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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