Methyl 4-bromo-2-methylbenzoate → Methyl 4-(cyclobutylmethyl)-2-methylbenzoate

HRID 541305Notes

Reaction equation

HRID 541305 reaction equation
[CH:1]1([C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:15]C)[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.Br[C:18]1C=CC(C(OC)=O)=C(C)C=1.C1(C[Mg]Br)CCC1.C1([Mg]Br)CCC1>>[CH:4]1([CH2:1][C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH3:15])[CH:6]=2)[CH2:3][CH2:2][CH2:18]1

Participants

5

Reactant 4

HCID 22031226Methyl 4-bromo-2-methylbenzoateHCID 68288811Methyl 4-cyclobutyl-2-ethylbenzoateHCID 178419648HCID 178419648, compoundHCID 178419658HCID 178419658, compound

Product 1

HCID 68288684Methyl 4-(cyclobutylmethyl)-2-methylbenzoateYield 84%

Procedure

The title compound (4.00 g, yellow oil, 84%) was prepared using a procedure similar to that used for the preparation of compound 181.3 using compound 152.1 (5.00 g) and cyclobutylmethylmagnesium bromide in place of compound 181.2 and cyclobutylmagnesium bromide respectively.

Sources & evidence

ORD record
ord-510d1ff8af134801b5152adace4e4b79
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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