Sodium Carbonate → 1-Bromo-2-(2-bromoethyl)benzene

HRID 1754947Notes

Reaction equation

HRID 1754947 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[Br:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32]CO.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Br:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][CH2:20][Br:24]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 27340892-(2-Bromophenyl)ethan-1-ol

Product 1

HCID 3340691-Bromo-2-(2-bromoethyl)benzeneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (7.83 g, 29.8 mmol) and carbon tetrabromide (12.4 g, 37.3 mmol) were added to a solution of 2-(2-bromophenyl)ethanol (5.00 g, 24.9 mmol) in dichloromethane (123 mL). The mixture was stirred at room temperature for 15 hours, and a saturated aqueous sodium carbonate solution was then added. The organic layer and the aqueous layer were separated, and the organic layer was then concentrated under reduced pressure. The resulting residue was triturated with ethyl acetate:n-hexane (1:4, 200 mL) and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 1-bromo-2-(2-bromoethyl)benzene as a colorless oil (6.23 g, 95%).

Workup

  1. customThe organic layer and the aqueous layer were separated
  2. concentrationthe organic layer was then concentrated under reduced pressure
  3. customThe resulting residue was triturated with ethyl acetate:n-hexane (1:4, 200 mL)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-65aad95bbdfa434dbb873b76d27c9e16
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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