Carbon tetrabromide → HCID 67468969, compound

HRID 1019745Notes

Reaction equation

HRID 1019745 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 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-chloro-5-methoxy-4-nitrophenyl)ethanol (0.85 g, 3.67 mmol) in DCM (20 mL), triphenylphosphine (1.54 g, 5.9 mmol) and carbon tetrabromide (1.46 g, 4.4 mmol) were added. The reaction mixture was maintained for 7 hours at room temperature then partitioned between water (50 mL) and EtOAc (80 mL). The separated aqueous phase was extracted with EtOAc (80 mL), then the combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure. The product was purified by column chromatography on neutral silica gel using 5-15% EtOAc in hexane to give the title compound (0.9 g, 83%) as a solid.

Workup

  1. customthen partitioned between water (50 mL) and EtOAc (80 mL)
  2. extractionThe separated aqueous phase was extracted with EtOAc (80 mL)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by column chromatography on neutral silica gel using 5-15% EtOAc in hexane

Sources & evidence

ORD record
ord-d0c6058e8f034612b58bc041950cde22
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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