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

HRID 1065748
Notes
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Reaction equation

HRID 1065748 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 24408BromineHCID 24437Sodium SulfiteHCID 130526961-(3-Benzyloxyphenyl)-1,1-dimethylheptane

Product 1

HCID 128821642-(Benzyloxy)-1-bromo-4-(2-methyloctan-2-YL)benzeneYield 80%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 6344DichloromethaneSolvent2×

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

  1. customTo a -78° C.
  2. additionadded to 500 ml
  3. extractionThe organic extract
  4. washis washed with two 500 ml
  5. dry with materialportions of saturated sodium bicarbonate, dried over magnesium sulfate
  6. customevaporated to an oil
  7. customThe crude product is purified via column chromatography on 500 g
  8. washof silica gel eluted with 10% ether-hexane
  9. customto give 41.9 g

Sources & evidence

ORD record
ord-609092929e3a4650816778afe95c9e5e
Source dataset
uspto-grants-1982_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04331602

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes