1-(4-BROMO-2-METHOXYPHENYL)-4-METHYL-1H-IMIDAZOLE synthesis

12synthesis methods

Product Name:1-(4-BROMO-2-METHOXYPHENYL)-4-METHYL-1H-IMIDAZOLE
CAS Number:870838-56-5
Molecular formula:C11H11BrN2O
Molecular Weight:267.12

958245-18-6 Synthesis

3-methoxy-4-(4-methylimidazole)benzenamine

958245-18-6
43 suppliers
$119.00/100mg

1-(4-BROMO-2-METHOXYPHENYL)-4-METHYL-1H-IMIDAZOLE

870838-56-5
14 suppliers
$245.43/5g

Yield:870838-56-5 91.3%

Reaction Conditions:

Stage #1: 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilinewith sulfuric acid;acetic acid;sodium nitrite at 10 - 20; for 0.5 h;
Stage #2: with hydrogen bromide;copper(I) bromide in water at 20; for 1 h;
Stage #3: with sodium carbonate in dichloromethane;water;

Steps:

A.A2.c

c) Preparation of intermediate 5 A stirred sol. OfNaNO₂ (7.47 g, 108 mmol) in cone. H₂SO₄ (160 ml) was cooled to 10 ⁰C. A sol. of intermediate 4 (20.0 g, 98.4 mmol) in AcOH (200 ml) was added at such a rate that the temperature of the r.m. was maintained below 10 ⁰C. After addition was completed, the ensuing r.m. was stirred at r.t. for 30 min. This sol. was added, dropwise, to a stirred sol. of CuBr (28.2 g, 196.8 mmol) in 48% HBr (200 ml) at r.t.The ensuing r.m. was stirred for 1 h, then diluted with 1 1 ice/H₂O. The resulting white precipitate was collected by filtration and washed with H₂O. (The mother liquor was treated as described below). The solid was then suspended in DCM/sat. aq. Na₂Cθ3 sol. and the resulting slurry filtered over dicalite. The o.l. of the filtrate was washed with diluted NH₄OH until the disappearance of blue colour. The organic phase was dried (MgSO/i), filtered and evaporated to give a brown solid. The mother liquor was basifed with solid Na₂CC^, then extracted with DCM. The combined organic extracts were washed with diluted NH₄OH until the disappearance of blue colour. The organic phase was dried (MgSOzi), filtered and evaporated to give a brown solid which was combined with the previously obtained solid. Yield: 24.0 g of intermediate 5 (91.3%).