Benzoyl Peroxide → HCID 59218436, compound

HRID 1675289Notes

Reaction equation

HRID 1675289 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]2([CH2:17][CH3:18])[CH2:15][CH3:16].CS(C1C=C(C=CC=1OC(F)(F)F)C[O:27][C:28]1[CH:33]=[CH:32][C:31]([C@@H:34]([C:39]2[CH:43]=[CH:42][O:41][N:40]=2)[CH2:35][C:36]([OH:38])=[O:37])=[CH:30][CH:29]=1)(=O)=O.C1C(=O)N(Br)C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:15]([C:6]1([CH2:17][CH3:18])[C:5]2[CH:4]=[C:3]([CH2:2][O:27][C:28]3[CH:33]=[CH:32][C:31]([C@@H:34]([C:39]4[CH:43]=[CH:42][O:41][N:40]=4)[CH2:35][C:36]([OH:38])=[O:37])=[CH:30][CH:29]=3)[CH:12]=[CH:11][C:10]=2[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7]1)[CH3:16]

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 57835884HCID 57835884, compoundHCID 59300572HCID 59300572, compound

Product 1

HCID 59218436HCID 59218436, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

6-(Bromomethyl)-4,4-diethyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (44.2) Starting material 44.1 was prepared according to the published procedure of Kim, C. et al. (Tetrahedron. Lett. 1994, 35 (19), 3017-3020). A mixture of 44.1 (0.5 g, 2.17 mmol), NBS (0.58 g, 3.25 mmol), and dibenzoyl peroxide (53 mg) in CCl4 (10 mL) was heated at reflux for 5 hours. The reaction was cooled, and the precipitate was filtered out. The solvent was removed providing crude 44.2, which was used directly in the next step.

Workup

  1. customwas prepared
  2. temperaturewas heated
  3. temperatureat reflux for 5 hours
  4. temperatureThe reaction was cooled
  5. filtrationthe precipitate was filtered out
  6. customThe solvent was removed
  7. customproviding crude 44.2, which

Sources & evidence

ORD record
ord-e4a193a1831841c2a7c07e79f45f3d40
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

Loading…