Acetic Acid → Bromomethyl 3-methoxyphenyl ketone

HRID 747313

Reaction equation

HRID 747313 reaction equation
[CH:1]1[C:10]2CCCC[C:5]=2[CH:4]=[CH:3][C:2]=1[C:11](=[O:13])[CH3:12].[C:14]([OH:17])(=O)C.[Br:18]Br>>[Br:18][CH2:12][C:11]([C:2]1[CH:3]=[CH:4][CH:5]=[C:10]([O:17][CH3:14])[CH:1]=1)=[O:13]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 698856-Acetyltetralin

Product 1

HCID 101294Bromomethyl 3-methoxyphenyl ketoneYield 28.9%

Procedure

Reaction of 1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (5 g, 28.70 mmol), acetic acid (1.6 mL, 28.70 mmol), and bromine (1.7 mL, 33.00 mmol) followed by recrystallisation from cold EtOAc/Hexane gave the title compound (1.9 g, 26%) as a yellow powder. 1H NMR (300 MHz, CD3OD) δ 1.84 (t, 4H, J=6.6 Hz), 2.80-2.85 (m, 4H), 4.61 (s, 2H), 7.19 (d, 1H, J=8.7 Hz), 7.70-7.78 (m, 2H). ES-MS m/z 253 (M+H).

Workup

  1. customfollowed by recrystallisation from cold EtOAc/Hexane

Sources & evidence

ORD record
ord-5335607b10a84cabb632b284682e8842
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Linked notes

Loading…