Carbon tetrabromide → HCID 67468969, compound

HRID 1019759Notes

Reaction equation

HRID 1019759 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13][CH2:14]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:36]>C(Cl)Cl>[Br:36][CH2:14][CH2:13][C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67469173HCID 67469173, compound

Product 1

HCID 67468969HCID 67468969, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(2-chloro-5-methoxy-4-nitrophenyl)ethanol (7.0 g, 30.22 mmol), triphenylphosphine (12.68 g, 48.3 mmol) and carbon tetrabromide (14.03 g, 42.3 mmol) in DCM (150 mL) was stirred at room temperature for 2 hours. The mixture was partitioned between water (150 mL) and EtOAc (100 mL), and then the separated aqueous phase was extracted with EtOAc (100 mL). The combined organic extracts were washed with water (80 mL), brine (80 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on neutral silica gel using 0-1% methanol in DCM to give the title compound (8.0 g, 90%) as a solid.

Workup

  1. customThe mixture was partitioned between water (150 mL) and EtOAc (100 mL)
  2. extractionthe separated aqueous phase was extracted with EtOAc (100 mL)
  3. washThe combined organic extracts were washed with water (80 mL), brine (80 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on neutral silica gel using 0-1% methanol in DCM

Sources & evidence

ORD record
ord-a69b0bc378644f0381fadba5a9476ad4
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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