Cyclohexanecarboxaldehyde → 2-(3-Bromophenyl)-1-cyclohexylethanol

HRID 1021133Notes

Reaction equation

HRID 1021133 reaction equation
[CH:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[CH2:13][Mg]Br>>[Br:9][C:10]1[CH:11]=[C:12]([CH2:13][CH:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[OH:8])[CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 16275CyclohexanecarboxaldehydeHCID 178419662HCID 178419662, compound

Product 1

HCID 607989922-(3-Bromophenyl)-1-cyclohexylethanol

Procedure

Grignard reaction between cyclohexanecarbaldehyde and 3-bromobenzyl magnesium bromide (0.25M in ether) gave 2-(3-bromophenyl)-1-cyclohexylethanol as a white solid. Yield (1.62 g, 23%): 1H NMR (400 MHz, DMSO-d6) δ 7.39 (d, J=0.8 Hz, 1H), 7.34-7.31 (m, 1H), 7.20-7.17 (m, 2H), 4.37 (d, J=6.0 Hz, 1H), 3.38-3.32 (m, 1H), 2.69 (dd, J=13.6, 3.6 Hz, 1H), 2.51-2.45 (dd, obs., 1H), 1.78-1.60 (m, 5H), 1.24-0.94 (m, 6H).

Sources & evidence

ORD record
ord-e6c3e36ee0c2490c89713e924ac593d9
Source dataset
uspto-grants-2014_05
Patent number
US08716529B2

Reaction notes

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