Carbon tetrabromide → HCID 58494024, compound

HRID 1942698Notes

Reaction equation

HRID 1942698 reaction equation
[Br:1][C:2]1[C:3]([CH2:10][CH3:11])=[C:4]([CH2:8]O)[CH:5]=[CH:6][CH:7]=1.C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][Br:13])[C:3]=1[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58494037HCID 58494037, compound

Product 1

HCID 58494024HCID 58494024, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-bromo-2-ethylphenyl)methanol (D133) (3 g, 13.95 mmol) in Dichloromethane (DCM) (50 mL) was added CBr4 (5.55 g, 16.74 mmol). To the reaction solution was added triphenylphosphine (5.49 g, 20.92 mmol) portionwise at 0° C. The reaction solution was warmed to room temperature and stirred at the temp overnight. The solvent was removed in vacuo and the residue was purified by ISCO column chromatography to afford 1-bromo-3-(bromomethyl)-2-ethylbenzene (D134) (1.3 g) as an oil.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by ISCO column chromatography

Sources & evidence

ORD record
ord-48a6910aa5964f68953a2524a5d48e0b
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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