Lithium diisopropylamide → 3-(2-Bromo-5-(cyclohexylmethoxy)phenyl)-3-hydroxypropanenitrile

HRID 875572Notes

Reaction equation

HRID 875572 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][C:3]=1[CH:4]=[O:5].[Li+].[CH3:19][CH:20]([N-:22]C(C)C)C>C(#N)C>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][C:3]=1[CH:4]([OH:5])[CH2:19][C:20]#[N:22]

Participants

4

Reactant 2

HCID 2724682Lithium diisopropylamideHCID 815895652-Bromo-5-(cyclohexylmethoxy)benzaldehyde

Product 1

HCID 673158873-(2-Bromo-5-(cyclohexylmethoxy)phenyl)-3-hydroxypropanenitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reaction of 2-bromo-5-(cyclohexylmethoxy)benzaldehyde with acetonitrile in the presence of LDA was conducted following the procedure given for Example 4 to give 3-(2-bromo-5-(cyclohexylmethoxy)phenyl)-3-hydroxypropanenitrile. Yield (0.49 g, 79%): 1H NMR (400 MHz, MeOD) δ 7.40 (d, J=8.8 Hz, 1H), 7.23 (d, J=2.8 Hz, 1H), 6.77 (dd, J=8.8, 2.4 Hz, 1H), 5.20 (dd, J=6.8, 4.4 Hz, 1H), 3.77 (d, J=6.8 Hz, 2H), 2.91 (dd, J=16.8, 4.0 Hz, 1H), 2.74 (dd, J=16.8, 6.8 Hz, 1H), 1.66-1.88 (m, 6H), 1.18-1.36 (m, 3H), 1.02-1.16 (m, 2H).

Sources & evidence

ORD record
ord-bde3cfd9d9ac4792aacaf4ddc24f7624
Source dataset
uspto-grants-2015_03
Patent number
US08981153B2

Reaction notes

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