Methyl 3-chloro-4-hydroxybenzoate → Methyl 3-chloro-4-isopropoxybenzoate

HRID 1809518Notes

Reaction equation

HRID 1809518 reaction equation
[Cl: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].Br[C:14]1[CH:15]=C(C=C(OC(C)C)[CH:23]=1)C(OC)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:14]([CH3:15])[CH3:23])[C:5]([O:7][CH3:8])=[O:6]

Participants

3

Reactant 2

HCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 53216693Methyl 3-bromo-5-isopropoxybenzoate

Product 1

HCID 22597811Methyl 3-chloro-4-isopropoxybenzoate

Procedure

Prepared from methyl 3-chloro-4-hydroxybenzoate according to the procedure for methyl 3-bromo-5-isopropoxybenzoate. LCMS-ESI (m/z) calculated for C11H13ClO3: 228.7; found 229.1 [M+H]+, tR=3.90 min. 1H NMR (400 MHz, CDCl3) δ 8.05 (d, J=2.1 Hz, 1H), 7.89 (dd, J=8.7, 2.2 Hz, 1H), 6.94 (d, J=8.8 Hz, 1H), 4.67 (dt, J=12.2, 6.1 Hz, 1H), 3.89 (s, 3H), 1.37 (dd, J=34.4, 30.1 Hz, 6H).

Sources & evidence

ORD record
ord-536ec1c555e64e09b670624909a07ee9
Source dataset
uspto-grants-2013_01
Patent number
US08362048B2

Reaction notes

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