2,2'-Bis(bromomethyl)-1,1'-binaphthyl → HCID 19080476, compound

HRID 964419Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([P:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[O:9]CC)=[CH:4][CH:3]=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>CC1C=CC=CC=1C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([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:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)=[O:9])([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 135 °C

Procedure

While stirring under nitrogen, 10.70 g (0.04 mol) of ethyl bis(4-fluorophenyl)phosphinite are added dropwise to a solution of 8.80 g (0.02 mol) of 2,2'-bis(bromo-methyl)-1,1'-binaphthyl in 40 ml of o-xylene, which solution has been heated to 135° C. After the end of the addition, the mixture is heated under reflux for a further 1.5 hours. After cooling to room temperature, the precipitated crystals are filtered off with suction and washed with xylene. This gives 14.1 g (94 %) of colorless crystals having a melting point of 211°-214° C.

Workup

additionAfter the end of the addition
temperaturethe mixture is heated
temperatureunder reflux for a further 1.5 hours
temperatureAfter cooling to room temperature
filtrationthe precipitated crystals are filtered off with suction
washwashed with xylene

Sources & evidence

ORD record: ord-89fdf0de39f34346b53b7874aa92289a
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05767317

Reaction notes

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