1,3-Dichloroacetone → 2-(4-Bromophenyl)-4-(chloromethyl)oxazole

HRID 1397423Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][CH2:12][C:13]([CH2:15]Cl)=O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][CH:15]=[C:13]([CH2:12][Cl:11])[N:8]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 107931,3-Dichloroacetone

HCID 696834-Bromobenzamide

Product 1

HCID 155551142-(4-Bromophenyl)-4-(chloromethyl)oxazoleYield 14%

Procedure

This compound was synthesized from 4-bromobenzamide and 1,3-dichloroacetone as described in example 74 step 1 (1.5 g, yield 14%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.92-7.89 (d, J=8.8 Hz, 2H), 7.71 (s, 1H), 7.61-7.59 (d, J=8.8 Hz, 2H), 4.57 (s, 2H). MS (ESI) m/z: Calculated for C10H7BrClNO: 272.94. found: 273.8 (M+H)+.

Sources & evidence

ORD record: ord-2e72f6c44e4d48ef9329c072765fddcf
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901156B2

Reaction notes

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