Dimethylformamide → HCID 18006169, compound

HRID 989438Notes

Reaction equation

HRID 989438 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[CH:11]([Br:13])[Br:12].CN(C=O)C.C(Cl)(=O)C([Cl:22])=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:22])=[O:7])=[CH:4][C:3]=1[CH:11]([Br:13])[Br:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 18006163HCID 18006163, compound

Product 1

HCID 18006169HCID 18006169, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 250 mL round bottom flask was charged with the 4-Bromo-3-(dibromomethyl)benzoic acid prepared as described above (114.6 g, 307 mmol) in anhydrous toluene (1.14 L) and anhydrous DMF (6.3 mL). The resulting suspension was stirred at RT under an argon atmosphere. Oxalyl chloride (29.5 mL, 338 mmol) was added dropwise. The reaction mixture became a clear yellow solution at the end of the reaction. HPLC indicated the reaction was complete in 2 hours. The solution was decanted away from a gummy oil deposited at the bottom of the reaction flask and the solution was concentrated on a rotary evaporator and then on a high vacuum pump overnight to dryness. The 4-Bromo-3-(dibromomethyl)benzoyl chloride was obtained as a light brown solid 115.02 g, 95.7% yield and area percent=93.5%. The 1H NMR spectrum was consistent with the assigned structure.

Workup

  1. customprepared
  2. customat the end of the reaction
  3. customThe solution was decanted away from a gummy oil
  4. concentrationthe solution was concentrated on a rotary evaporator
  5. customon a high vacuum pump overnight

Sources & evidence

ORD record
ord-9cf4a9f0e5fd4ce291bd9f2a5ad462e2
Source dataset
uspto-grants-2003_10
Patent number
US06639082B2

Reaction notes

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