Diethyl Ether → 2-((3-(Bromomethyl)phenoxy)methyl)-7-chloroquinoline

HRID 258466Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20]O)[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:23].C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOCC>C(Cl)Cl>[Br:23][CH2:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[O:13][CH2:12][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To the benzylic alcohol of Step 2 (47.0 g, 157 mmol) and CBr4 (60.08 g, 181 mmol) in CH2Cl2 (750 mL) at 0° C., a solution of 1,2-bis(diphenylphosphino) ethane (DIPHOS, 36.29 g, 91.1 mmol) in CH2Cl2 (350 mL) was added and the resulting mixture was stirred at 0° C. for 45 min. and at r.t. for 30 min. Ether was then added and the mixture was filtered through a pad of silica and the silica was washed with EtOAc:toluene 20:80 to yield 40.35 g (70%) of the pure title compound.

Workup

filtrationthe mixture was filtered through a pad of silica
washthe silica was washed with EtOAc:toluene 20:80

Sources & evidence

ORD record: ord-6f0f13cfba04407a9599fd19128a29e3
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05266568

Reaction notes

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