Tert-Butylamine → 2-(Benzyloxy)-1-bromo-4-(2-methyloctan-2-YL)benzene

HRID 2199010Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N)(C)(C)C.[Br:29]Br.S([O-])([O-])=O.[Na+].[Na+]>CCOCC.ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH3:22])([CH3:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:12]=[CH:13][C:14]=1[Br:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a -78° C. solution of 42.6 g. (0.134 mole) of 1-benzyloxy-3-(1,1-dimethylheptyl)benzene and 12.2 g. (0.200 mole) of t-butylamine in 300 ml. of dichloromethane was added a solution of 27.2 g. (0.151 mole), bromine in 100 ml. of dichloromethane. The reaction mixture was then allowed to warm to 25° C. and added to 500 ml. saturated sodium sulfite and 500 ml. ether. The organic extract was washed with two 500 ml. portions of saturated sodium bicarbonate, dried over magnesium sulfate and evaporated to an oil. The crude product was purified via column chromatography on 500 g. of silica gel eluted with 10% ether-hexane to give 41.9 g. (80%) of the title compound as an oil.

Workup

customTo a -78° C.
additionadded to 500 ml
extractionThe organic extract
washwas washed with two 500 ml
dry with materialportions of saturated sodium bicarbonate, dried over magnesium sulfate
customevaporated to an oil
customThe crude product was purified via column chromatography on 500 g
washof silica gel eluted with 10% ether-hexane
customto give 41.9 g

Sources & evidence

ORD record: ord-e4d8fd7910d34a89aae7aac7fb987f75
Source dataset: uspto-grants-1982_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04360700

Reaction notes

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