4-Bromo-1-methoxy-2-methylbenzene → (3-Bromo-5-cyclopropylmethoxy-phenyl)-(4-methoxy-3-methyl-phenyl)methanone

HRID 1668756Notes

Reaction equation

HRID 1668756 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)[CH:13]=1)[C:5](N(OC)C)=[O:6].Br[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([CH3:28])[CH:21]=1>>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([CH3:28])[CH:21]=2)=[O:6])[CH:11]=[C:12]([O:14][CH2:15][CH:16]2[CH2:17][CH2:18]2)[CH:13]=1

Participants

3

Reactant 2

HCID 6083154-Bromo-1-methoxy-2-methylbenzeneHCID 578250753-bromo-5-cyclopropylmethoxy-N-methoxy-N-methyl-benzamide

Product 1

HCID 57825246(3-Bromo-5-cyclopropylmethoxy-phenyl)-(4-methoxy-3-methyl-phenyl)methanoneYield 76%

Procedure

In analogy to the procedure described for the preparation of the Building Block AU, the reaction of the 3-bromo-5-cyclopropylmethoxy-N-methoxy-N-methyl-benzamide and 4-bromo-1-methoxy-2-methyl-benzene, beforehand transformed to the Grignard reagent, yielded the title compound as a colourless oil (yield: 76% of theory). Mass (calculated) C19H19BrO3 [374]; (found) [M+H]+=375, 377.

Workup

  1. customIn analogy to the procedure described for the preparation of the Building Block AU

Sources & evidence

ORD record
ord-de0e4c8ef00646c58dc2da8fd17a18a1
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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