Carbon tetrabromide → HCID 69041083, compound

HRID 1726531Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:50]=[C:49](/[CH:51]=[CH:52]/[C:53]([O:55][CH3:56])=[O:54])[CH:48]=[CH:47][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[C:41](=[O:44])[O:42][CH3:43])=[CH:35][C:34]=2[O:45][CH3:46])[CH:22]=1)[CH2:18]O.[Br:57]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3]1[CH:50]=[C:49](/[CH:51]=[CH:52]/[C:53]([O:55][CH3:56])=[O:54])[CH:48]=[CH:47][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[C:41](=[O:44])[O:42][CH3:43])=[CH:35][C:34]=2[O:45][CH3:46])[CH:22]=1)[CH2:18][Br:57]

Participants

Conditions

Temperature: 0 °C

Procedure

2.39 g (3.08 mmol) of 3,5-bis[(8-{2-methoxy-4-[(1E)-3-methoxy-3-oxo-1-propenyl]phenoxy}octyl)oxy]benzyl alcohol, 1,14 g (3.42 mmol) tetrabromomethane were dissolved in 25 ml dichloromethane. The solution was subsequently cooled to 0° C. and a solution of 0.86 g (3.29 mmol) triphenylphosphine in 20 ml dichloromethane was added dropwise thereto over a period of 1 hour. The mixture was subsequently allowed to react for 20 h at 25° C. and reduced in volume by evaporation. Chromatography of the residue on 120 g silica gel using first toluene:ethyl acetate (19:1) then (4:1) as eluant yielded 1.94 g (78%) 3,5-bis[(8-{2-methoxy-4-[(1E)-3-methoxy-3-oxo-1-propenyl]phenoxy}octyl)oxy]benzyl bromide as colorless oil.

Workup

customto react for 20 h at 25° C.
customreduced in volume by evaporation

Sources & evidence

ORD record: ord-2a725ff3b0914ee0a1db8b3dbc50bcf8
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491752B2

Reaction notes

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