Bromomethylcyclopropane → Methyl 3-bromo-4-(cyclopropylmethoxy)benzoate

HRID 1809520Notes

Reaction equation

HRID 1809520 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[CH:13]1([CH2:16]Br)[CH2:15][CH2:14]1.BrC1C=C(C=C(OC(C)C)C=1)C(OC)=O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH2:16][CH:13]1[CH2:15][CH2:14]1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 4778958Methyl 3-bromo-4-hydroxybenzoateHCID 53216693Methyl 3-bromo-5-isopropoxybenzoate

Product 1

HCID 67194639Methyl 3-bromo-4-(cyclopropylmethoxy)benzoate

Procedure

Prepared from methyl 3-bromo-4-hydroxybenzoate and cyclopropylmethylbromide according to the procedure for methyl 3-bromo-5-isopropoxybenzoate. LCMS-ESI (m/z) calculated for C12H13BrO3: 285.1; no m/z observed, tR=3.96 min. 1H NMR (400 MHz, CDCl3) δ 8.22 (t, J=2.8 Hz, 1H), 8.02-7.88 (m, 1H), 6.91-6.81 (m, 1H), 4.02-3.91 (m, 2H), 3.88 (d, J=5.5 Hz, 3H), 1.41-1.26 (m, 1H), 0.76-0.59 (m, 2H), 0.52-0.31 (m, 2H).

Sources & evidence

ORD record
ord-db90c086471b4bc499d30ffb05006cfe
Source dataset
uspto-grants-2013_01
Patent number
US08362048B2

Reaction notes

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