Ethyl Bromide → HCID 19080477, compound

HRID 964418Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

While stirring under nitrogen, 8.8 g (33 mmol) of ethyl bis(3-fluorophenyl)phosphinite are slowly added dropwise to a solution of 7.27 g (16.6 mmol) of 2,2'-bis(bromo-methyl)-1,1'-binaphthyl in 40 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 11.5 g (91 %) of colorless crystals having a melting point of 280°-284° 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-e97fc17a39734e5697d130e857d13f50
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05767317

Reaction notes

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