Ethyl formate → N-(4-bromo-3-methyl-benzyl)-formamide

Reaction equation

[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][C:3]=1[CH3:10].C(N(CC)CC)C.[CH:18](OCC)=[O:19]>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][CH:18]=[O:19])=[CH:4][C:3]=1[CH3:10]

Participants

Reactant 3

HCID 8025Ethyl formate

HCID 8471Triethylamine

HCID 21756143(4-Bromo-3-methylphenyl)methanamine

Product 1

HCID 58497978N-(4-bromo-3-methyl-benzyl)-formamide

Procedure

To a solution of 4-bromo-3-methyl-benzylamine (Example 10.1) (15.11 g) in ethyl formate (150 ml) was added triethylamine (1.5 ml) at ambient temperature. The reaction mixture was stirred at reflux for 16 hours. The reaction mixture was concentrated and the residue was triturated with diisopropyl ether/heptane (1:1) (100 ml) to give N-(4-bromo-3-methyl-benzyl)-formamide (14.04 g) as a white solid. 1H-NMR (400 MHz, CDCl3): 8.28 (s, 1H), 7.49 (m, 1H), 7.16 (s, 1H), 6.97 (m, 1H), 5.85 (s, 1H), 4.42 (m, 2H), 2.39 (s, 3H) ppm.

Workup

temperatureat reflux for 16 hours
concentrationThe reaction mixture was concentrated
customthe residue was triturated with diisopropyl ether/heptane (1:1) (100 ml)

Sources & evidence

ORD record: ord-655b2fb77cc04ca4953a5d16062fe106
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216973B2

Reaction notes

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