Carbon tetrabromide → HCID 22236580, compound

HRID 1743854Notes

Reaction equation

HRID 1743854 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:34]>C(Cl)Cl>[Br:34][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22236583HCID 22236583, compound

Product 1

HCID 22236580HCID 22236580, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-fluoro-2-nitro-phenyl)-ethanol (20.7, 0.11 mole) in methylene chloride (500 mL) was added triphenylphosphine (30.0 g, 0.11 mole) and the mixture was cooled to 0° C. Carbon tetrabromide (40.0 g, 0.12 mole) in methylene chloride (100 mL) was added dropwise through an addition funnel. The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue purified by flash column chromatography (silica gel, ethyl acetate:hexanes 3:7) to provide 24.0 g of the title compound as a yellow solid. 1H NMR (CDCl3): 7.70 δ (d, 1H); 7.40 δ (dd, 1H); 7.30 δ (d of t, 1H); 3.65 δ (t, 2H); 3.40 δ (t, 2H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash column chromatography (silica gel, ethyl acetate:hexanes 3:7)

Sources & evidence

ORD record
ord-3938eccebae1417c8529a27f927a6531
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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