Bromocyclopentane → 4-Cyclopentyloxydibenzo[b,d]furan

HRID 1293433Notes

Reaction equation

HRID 1293433 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([OH:14])=[CH:3][CH:2]=1.[CH:15]1(Br)[CH2:19][CH2:18][CH2:17][CH2:16]1.[H-].[Na+]>>[CH:15]1([O:14][C:4]2[C:5]3[O:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=[CH:2][CH:3]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 30150514-Dibenzofuranol

Product 1

HCID 692801164-Cyclopentyloxydibenzo[b,d]furanYield 92%

Procedure

Reaction of dibenzo[b,d]furan-4-ol (1 g, 5.43 mmol) with cyclopentyl bromide (1.60 g, 10.86 mmol) in the presence of 60% sodium hydride (326 mg, 8.12 mmol), gave 1.25 g (92%) of the product as viscous liquid, IR (neat) 2957, 2870, 1449, 1269, 1193 cm−1. 1H NMR (300 MHz, CDCl3) δ 1.57-1.72 (m, 2H), 1.84-1.89 (m, 2H), 1.93-2.04 (m, 4H), 5.01 (quint., 1H), 6.97 (d, J=8.1 Hz, 1H), 7.22 (t, J=7.9 Hz, 1H), 7.30 (t, J=8.1 Hz, 1H), 7.45 (t, J=8.1 Hz, 1H), 7.51 (d, J=7.8 Hz, 1H), 7.60 (d, J=8.2 Hz, 1H), 7.89 (d, J=8.1 Hz, 1H).

Sources & evidence

ORD record
ord-638ccf1a65b3475eb6e525db02b635a9
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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