Carbon tetrabromide → 5-(Bromomethyl)-2-[2-(3-methoxypropyl)phenyl]-4-(trifluoromethyl)pyridine

HRID 2194898Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:17]=[CH:16][C:15]([CH2:18]O)=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=1.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:53]>C(Cl)Cl.CCOC(C)=O>[Br:53][CH2:18][C:15]1[C:14]([C:20]([F:23])([F:22])[F:21])=[CH:13][C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[N:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [6-[2-(3-methoxypropyl)phenyl]-4-(trifluoromethyl)pyridin-3-yl]methanol (1 eq.) from step 2, in CH2Cl2 (0.1M) at 0° C. was added 1-2 bis(diphenylphosphine)ethane (1 eq.) the CBr4 (1 eq.). The mixture was stirred at 0° C. for 45 min, diluted with Hex/EtOAc 10%, filtered in celite and concentrated afforded the desired compound as an oil.

Workup

filtrationfiltered in celite
concentrationconcentrated

Sources & evidence

ORD record: ord-dcddd9629eb840f9b766eb5790692cff
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334308B2

Reaction notes

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