Carbon tetrabromide → HCID 67809812, compound

HRID 128791Notes

Reaction equation

HRID 128791 reaction equation
[CH3:1]/[C:2](=[CH:5]\[CH2:6][C:7]1[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][CH2:9][C:8]=1[CH3:15])/[CH2:3]O.[Br:16]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:16][CH2:3]/[C:2](/[CH3:1])=[CH:5]/[CH2:6][C:7]1[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][CH2:9][C:8]=1[CH3:15]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5369482HCID 5369482, compound

Product 1

HCID 67809812HCID 67809812, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenol (Chem. Abstr., 94, 65904 h) (4.15 g) and tetrabromomethane (7.0 g) in dichloromethane (40 ml) is added over 20 min a solution of triphenylphosphine (5.51 g) in dichloromethane (30 ml). The mixture is stirred overnight under nitrogen, the solvent is removed, and the residue is triturated with hexane. The mixture is filtered, and the filtrate concentrated in vacuo to provide (2E)-1-bromo-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butene (5.25 g) as an orange oil.

Workup

  1. customthe solvent is removed
  2. customthe residue is triturated with hexane
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-4153fff4d7a1414895bf633d014d4b0a
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Reaction notes

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