N-bromobutanimide → 6-(Bromomethyl)-1,1,4,4-Tetramethyl-1,2,3,4-Tetrahydronaphthalene

HRID 2076429Notes

Reaction equation

HRID 2076429 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[CH:6]([CH2:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[C:5]([CH3:14])([CH3:13])[CH2:4][CH2:3]1.[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:16][CH2:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([CH3:15])([CH3:1])[CH2:3][CH2:4][C:5]2([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 86612828HCID 86612828, compound

Product 1

HCID 27355976-(Bromomethyl)-1,1,4,4-Tetramethyl-1,2,3,4-TetrahydronaphthaleneYield 386.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
84 °C

Procedure

A solution of 1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalene 1 (2.00 g, 9.88 mmol), N-bromosuccinimide (1.85 mmol, 10.37 mmol), benzoyl peroxide (91 mg, 0.28 mmol) in 35 mL of CCl4 was heated at reflux (84° C., oil bath) for 2.5 h. After cooling top room temperature, the solution was concentrated in vacuo. Diethyl ether (100 mL) was added and the solution was filtered (to remove the succinimide formed) and concentrated to give a crude oil. The crude oil was purified by silica gel column chromatography using as eluent petroleum ether. 6-(Bromomethyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene 8 (2.01 g, 72.5% yield) was obtained as a colourless oil.

Workup

  1. temperatureAfter cooling top room temperature
  2. concentrationthe solution was concentrated in vacuo
  3. additionDiethyl ether (100 mL) was added
  4. filtrationthe solution was filtered (
  5. customto remove the succinimide
  6. customformed) and
  7. concentrationconcentrated
  8. customto give a crude oil
  9. customThe crude oil was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c8fd3d5945a94e40ab689b24b9a7a650
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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