3-Bromobenzyl bromide → 1-(3-Bromo-benzyl)-7-trifluoromethyl-1,2,3,4-tetrahydro-quinoline

HRID 1782680Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[CH:3]=1.[F:10][C:11]([F:23])([F:22])[C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH2:18][NH:19]2)=[CH:14][CH:13]=1.C([O-])(=O)C.[Na+]>C(O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][N:19]1[C:20]2[C:15](=[CH:14][CH:13]=[C:12]([C:11]([F:10])([F:22])[F:23])[CH:21]=2)[CH2:16][CH2:17][CH2:18]1

Participants

Conditions

Temperature: 80 °C

Procedure

Under a nitrogen atmosphere, a solution of bromo-3-bromomethyl-benzene (3.47 g, 13.p mmol) and 7-trifluoromethyl-1,2,3,4-tetrahydro-quinoline (2.93 g, 14.6 mmol) in ethanol (15 mL, 1 M) was treated with sodium acetate (5.69 g, 69.3 mmol) and heated to 80° C. After stirring 2 h, the solution was cooled to room temperature, diluted with water, extracted with ethyl acetate and washed with saturated aq sodium chloride. The organic layer was dried over MgSO4, filtered and concentrated. Purification by column chromatography (10% ethyl acetate in heptane) provided 1-(3-bromo-benzyl)-7-trifluoromethyl-1,2,3,4-tetrahydro-quinoline 4.21 g (82%) as a colorless oil.

Workup

temperaturethe solution was cooled to room temperature
extractionextracted with ethyl acetate
washwashed with saturated aq sodium chloride
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customPurification by column chromatography (10% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-b2cd2207d0084987a974d1c5932b137e
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498356B2

Reaction notes

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