3-Bromo-4-(bromomethyl)benzonitrile → tert-butyl N-(2-bromo-4-cyanobenzyl)-N-methylglycinate

HRID 2404310Notes

Reaction equation

HRID 2404310 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:3]=1[CH2:4]Br.Cl.[C:13]([O:17][C:18](=[O:22])[CH2:19][NH:20][CH3:21])([CH3:16])([CH3:15])[CH3:14]>>[Br:1][C:2]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:3]=1[CH2:4][N:20]([CH3:21])[CH2:19][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:22]

Participants

3

Reactant 2

HCID 2884363-Bromo-4-(bromomethyl)benzonitrileHCID 11252350Sarcosine t-butyl ester hydrochloride

Product 1

HCID 66678124tert-butyl N-(2-bromo-4-cyanobenzyl)-N-methylglycinate

Procedure

The title compound was prepared following the general procedure 10, starting from 2-bromo-4-cyanobenzyl bromide (Carbocor) and sarcosine tert-butyl ester hydrochloride. It was obtained as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.17 (d, J=1.6 Hz, 1H), 7.88 (dd, J=8.0, 1.6 Hz, 1H), 7.69 (d, J=8.0 Hz, 1H), 3.82 (s, 2H), 3.31 (s, 2H), 2.31 (s, 3H), 1.43 (s, 9H). LC/MS (Method B): 338.9, 340.9 (M+H)+. HPLC (Method A) Rt 3.10 min (Purity: 99.6%).

Workup

  1. customIt was obtained as a white solid

Sources & evidence

ORD record
ord-62a56fec43df4594bebd190f749ed425
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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