Carbon tetrabromide → HCID 86628049, compound

HRID 2078425Notes

Reaction equation

HRID 2078425 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][CH2:12][CH2:13]O)=[CH:5][CH:4]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>C(Cl)Cl>[Br:35][CH2:13][CH2:12][O:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 13208939HCID 13208939, compound

Product 1

HCID 86628049HCID 86628049, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[2-(4-cyanophenyl)ethoxy]ethanol (4.3 g, 0.0225 mol; see step (iv) above) in DCM (50 mL), triphenylphosphine (11.8 g, 0.045 mol) was added. The resulting mixture was stirred for 15 min and cooled to between 0 and 5° C. A solution of CBr4 (14.9 g, 0.045 mol) in DCM (25 mL) was added dropwise and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the crude product was purified by column chromatography (silica gel: 60-120 mesh, petroleum ether: ethyl acetate (70:30) eluent) to provide the title compound (yield: 4.8 g, 84%).

Workup

  1. temperaturecooled to between 0 and 5° C
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. concentrationThe reaction mixture was concentrated
  4. customthe crude product was purified by column chromatography (silica gel: 60-120 mesh, petroleum ether: ethyl acetate (70:30) eluent)

Sources & evidence

ORD record
ord-45832775836544f39c6cab0c321807d6
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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