Diethyl Ether → HCID 86632160, compound

HRID 1484133Notes

Reaction equation

HRID 1484133 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:20]([O:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH3:33])[C:24]=1[CH2:25][Br:26])[CH3:21].C(OCC)C>C1(C)C=CC=CC=1>[Br-:26].[CH2:32]([O:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:23]([O:22][CH2:20][CH3:21])[C:24]=1[CH2:25][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:33]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 68941966HCID 68941966, compound

Product 1

HCID 86632160HCID 86632160, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of triphenylphosphine (1.31 g, 5.01 mmol) in toluene (6.5 mL) was added 2,6-diethoxybenzyl bromide (1.3 g, 5.01 mmol) and the mixture stirred at room temperature overnight. Diethyl ether was added and the solid was collected by filtration to give (2,6-diethoxybenzyl)triphenylphosphonium bromide as an off-white solid. Yield (1.58 g, 60%): 1H NMR (400 MHz, DMSO-d6) δ 7.83-7.87 (m, 3H), 7.68 (ddd, J=7.6, 7.6, 3.2 Hz, 6H), 7.55 (d, J=7.6 Hz, 3H), 7.52 (d, J=7.2 Hz, 3H), 7.18 (ddd, J=8.4, 8.4, 2.4 Hz, 1H), 6.45 (d, J=8.4 Hz, 2H), 4.66 (d, J=14.0 Hz, 2H), 3.65 (q, J=6.8 Hz, 4H), 1.01 (t, J=6.8 Hz, 6H).

Workup

  1. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-bca449ee512945f1ba959c3b66424c04
Source dataset
uspto-grants-2016_08
Patent number
US09421210B2

Reaction notes

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