Hexane → HCID 86665739, compound

HRID 1191647Notes

Reaction equation

HRID 1191647 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([N+:12]([O-:14])=[O:13])=[C:8]([CH:11]=1)[CH:9]=O)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34](Br)(Br)([Br:36])[Br:35].CCCCCC>ClCCl>[Br:35][C:34]([Br:36])=[CH:9][C:8]1[CH:11]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 8058HexaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 20200496HCID 20200496, compound

Product 1

HCID 86665739HCID 86665739, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-ethoxy-2-nitrobenzaldehyde (519 mg) and triphenylphosphine (2.09 g) in dichloromethane (13 mL) was added a solution of carbon tetrabromide (1.32 g) in dichloromethane in three minutes under cooling with ice, and the mixture was stirred overnight at room temperature. Hexane (20 mL) was added to the reaction mixture, and this resulting mixture was stirred for 10 minutes and then filtered through silica gel. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (712 mg).

Workup

  1. temperatureunder cooling with ice
  2. stirringthis resulting mixture was stirred for 10 minutes
  3. filtrationfiltered through silica gel
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-fcde38261e474619851137206c1d0e68
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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