2-Bromopropane → 2-(1-Admantyl)-4-iodo-1-(octyloxy)benzene

HRID 710460Notes

Reaction equation

HRID 710460 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].BrC(C)C.[C:14]12([C:24]3[CH:29]=[C:28]([I:30])[CH:27]=[CH:26][C:25]=3[OH:31])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.C12(C3C=C(C=CC=3O)C=O)CC3CC(CC(C3)C1)C2>>[C:14]12([C:24]3[CH:29]=[C:28]([I:30])[CH:27]=[CH:26][C:25]=3[O:31][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:15][CH:16]3[CH2:22][CH:20]([CH2:19][CH:18]([CH2:17]3)[CH2:23]1)[CH2:21]2

Participants

5

Reactant 4

HCID 63582-BromopropaneHCID 81401-BromooctaneHCID 34078923-(1-Admantyl)-4-hydroxybenzaldehydeHCID 532612032-(1-Admantyl)-4-iodo-phenol

Product 1

HCID 667264002-(1-Admantyl)-4-iodo-1-(octyloxy)benzeneYield 72%

Procedure

When 1-bromooctane was substituted for 2-bromopropane and 2-(1-admantyl)-4-iodo-phenol was substituted for 3-(1-admantyl)-4-hydroxybenzaldehyde in Example 60, Step A, the identical process afforded the title compound in 72% yield. 1H-NMR (CDCl3) 0.87 (tr, 3H, J=5.22 Hz); 1.26-1.29 (m, 9H); 1.51-1.53 (m, 2H); 1.75 (s, 6H); 1.81-1.86 (m, 2H); 2.07 (5, 9H); 3.91 (tr, 2H, J=6.28 Hz); 6.58-6.6 (d, 1H, J=8.21 Hz); 7.39-7.42r(m, 2H).

Sources & evidence

ORD record
ord-f72ef9a547514bccbc7f9d29e4cf6dff
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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