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

HRID 2107357Notes

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 is added a solution of 27.2 g. (0.151 mole), bromine in 100 ml. of dichloromethane. The reaction mixture is then allowed to warm to 25° C. and added to 500 ml. saturated sodium sulfite and 500 ml. ether. The organic extract is washed with two 500 ml. portions of saturated sodium bicarbonate, dried over magnesium sulfate and evaporated to an oil. The crude product is 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
washis washed with two 500 ml
dry with materialportions of saturated sodium bicarbonate, dried over magnesium sulfate
customevaporated to an oil
customThe crude product is 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-ccc68333fcb24699852f7dde94cb66ef
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04933475

Reaction notes

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