1-(Difluoromethoxy)-4-ethynylbenzene → 1-Butyl-3-{[4-(difluoromethoxy)phenyl]ethynyl}benzene

HRID 30557

Reaction equation

HRID 30557 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][CH3:11])[CH:3]=1.[F:12][CH:13]([F:23])[O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]#[CH:22])=[CH:17][CH:16]=1>>[CH2:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:22]#[C:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH:13]([F:23])[F:12])=[CH:16][CH:17]=2)[CH:3]=1)[CH2:9][CH2:10][CH3:11]

Participants

3

Reactant 2

HCID 27784971-(Difluoromethoxy)-4-ethynylbenzeneHCID 139541021-Bromo-3-butylbenzene

Product 1

HCID 574358601-Butyl-3-{[4-(difluoromethoxy)phenyl]ethynyl}benzene

Procedure

Using essentially the same procedure described in Example 1, step a, and employing 1-bromo-3-butylbenzene and 1-(difluoromethoxy)-4-ethynylbenzene, the phenylethynylbenzene product was obtained. This product was purified on silica gel (Biotage) using hexanes/EtOAc 50/1 as the eluting solvents to give 1-butyl-3-{[4-(difluoromethoxy)phenyl]ethynyl}benzene as a colorless oil (0.56 g, 28% yield), MS m/e M+ 300; 1H NMR (400 MHz, DMSO-d6) 0.82 (t, J=7.19 Hz, 3H), 1.25 (m, 2H), 1.55 (m, 2H), 2.56 (t, J=7.56 Hz, 2H), 7.2 (m, 3H), 7.35-7.45 (m, 4H), 7.58 (d, J=8.79 Hz, 2H).

Sources & evidence

ORD record
ord-ef3dcaa71b4b406faed3b6f663c3af0f
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Linked notes

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