Cyclohexane, (bromomethyl)- → Ethyl 3-bromo-5-(cyclohexylmethoxy)benzoate

HRID 74429Notes

Reaction equation

HRID 74429 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([OH:13])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([O:13][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

3

Reactant 2

HCID 137636Cyclohexane, (bromomethyl)-HCID 11708561ethyl 3-bromo-5-hydroxybenzoate

Product 1

HCID 67317627Ethyl 3-bromo-5-(cyclohexylmethoxy)benzoate

Procedure

Alkylation of ethyl 3-bromo-5-hydroxybenzoate using (bromomethyl)cyclohexane gave ethyl 3-bromo-5-(cyclohexylmethoxy)benzoate. Yield (1.36 g, 100%): 1H NMR (400 MHz, CDCl3) δ 7.72 (t, J=1.6 Hz, 1H), 7.46 (dd, J=2.4, 1.2 Hz, 1H), 7.20 (dd, J=2.4, 1.6 Hz, 1H), 4.35 (q, J=7.2 Hz, 2H), 3.76 (d, J=6.4 Hz, 2H), 1.67-1.88 (m, 6H), 1.38 (t, J=7.2 Hz, 3H), 1.16-1.32 (m, 3H), 1.01-1.11 (m, 2H).

Sources & evidence

ORD record
ord-bcdd01b61dce4d95b5d273027497797e
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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