Carbon tetrabromide → HCID 86665744, compound

HRID 1191657Notes

Reaction equation

HRID 1191657 reaction equation
[F:1][CH:2]([F:15])[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.[C:16](Br)(Br)([Br:18])[Br:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:17][C:16]([Br:18])=[CH:9][C:8]1[CH:11]=[C:4]([O:3][CH:2]([F:15])[F:1])[CH:5]=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86665743HCID 86665743, compound

Product 1

HCID 86665744HCID 86665744, compoundYield 131.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-difluoromethoxy-2-nitrobenzaldehyde (238 mg) and carbon tetrabromide (545 mg) in dichloromethane (5.4 mL) was added dropwise a solution of triphenylphosphine (863 mg) in dichloromethane (3.6 mL) under cooling with ice. The mixture was gradually warmed to room temperature and stirred for 6 hours. The reaction mixture was concentrated under reduced pressure. The residue was suspended in diethyl ether and this resulting mixture was stirred at room temperature for 16 hours. The precipitate was removed by filtration through celite (registered trademark) and washed with diethyl ether. The filtrate was concentrated under reduced pressure to obtain the title compound (536 mg).

Workup

  1. temperatureunder cooling with ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. stirringthis resulting mixture was stirred at room temperature for 16 hours
  4. customThe precipitate was removed by filtration through celite (registered trademark)
  5. washwashed with diethyl ether
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f4f341e545684b569b134af83e33f977
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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