Ethyl Bromide → HCID 19080480, compound

HRID 964420Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[P:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[O:9]CC.Br[CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]=1[C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[CH2:41]Br.[CH2:43](Br)[CH3:44]>CC1C=CC=CC=1C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[P:8]([CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]=1[C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[CH2:41][P:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:9])([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:43]=1[CH3:44])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

While stirring under nitrogen, 21.5 g (83 mmol) of ethyl bis(2-methylphenyl)phosphinite are slowly added dropwise to a solution of 18.4 g (42 mmol) of 2,2'-bis(bromo-methyl)-1,1'-binaphthyl in 100 ml of o-xylene, which solution has been heated to 120° C., with ethyl bromide distilling off. After the end of the addition, the mixture is heated under reflux for a further two hours and is then cooled to 0° C. The solid is filtered off, washed with cold o-xylene and dried in vacuo. This gives 25.1 g (81%) of colorless crystals having a melting point of 231°-234° C.

Workup

additionAfter the end of the addition
temperaturethe mixture is heated
temperatureunder reflux for a further two hours
filtrationThe solid is filtered off
washwashed with cold o-xylene
customdried in vacuo

Sources & evidence

ORD record: ord-23aba350f16a42dbb1d18f9814802cf1
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05767317

Reaction notes

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