Carbon tetrabromide → 2-Nitrophenethyl bromide

HRID 2378930Notes

Reaction equation

HRID 2378930 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:20]([C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[CH2:25][CH2:26]O)([O-:22])=[O:21].C(Br)(Br)(Br)[Br:33]>ClCCl>[Br:33][CH2:26][CH2:25][C:24]1[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=1[N+:20]([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 270542-Nitrophenethyl alcohol

Product 1

HCID 123638782-Nitrophenethyl bromideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triphenylphosphine (6.60 g, 25.2 mmol) was dissolved in dichloromethane (75 ml). Mixture was cooled to 0° C. 2-Nitrophenethyl alcohol (3.0 ml, 21.36 mmol) was added to the mixture drop-wise. A solution of carbon tetrabromide (8.50 g, 25.6 mmol) in 5 mL dichloromethane was added to the reaction mixture drop-wise. Reaction stirred at 0° C. for 45 minutes. Mixture was concentrated by roto-vap. Residue was treated with 100 mL diethyl ether. Solids were filtered off, washed with diethyl ether and discarded. Filtrate was concentrated. Silica gel chromatography on the residue eluting ethyl acetate-hexanes afforded the title compound as yellow oil in 81% yield. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 7.97 (d, J=8.05 Hz, 1 H) 7.49-7.68 (m, 1 H) 7.41 (t, J=7.68 Hz, 2 H) 3.66 (t, J=6.77 Hz, 2 H) 3.43 (t, J=7.14 Hz, 2 H).

Workup

  1. customReaction
  2. concentrationMixture was concentrated by roto-vap
  3. additionResidue was treated with 100 mL diethyl ether
  4. filtrationSolids were filtered off
  5. washwashed with diethyl ether
  6. concentrationFiltrate was concentrated
  7. washSilica gel chromatography on the residue eluting ethyl acetate-hexanes

Sources & evidence

ORD record
ord-0cd4575cc8674a219f415dca2510d969
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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