Tetrafluoroboric acid → 1-Bromo-4-fluoro-2,5-dimethylbenzene

HRID 988935Notes

Reaction equation

HRID 988935 reaction equation
N[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][C:3]=1[CH3:10].[F:11][B-](F)(F)F.[H+].N([O-])=O.[Na+]>O>[Br:9][C:5]1[CH:4]=[C:3]([CH3:10])[C:2]([F:11])=[CH:7][C:6]=1[CH3:8]

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 81671304-Bromo-2,5-dimethylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 135534141-Bromo-4-fluoro-2,5-dimethylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

373 g of 2-amino-5-bromo-p-xylene were suspended in 1860 ml of H2O in a 4 l four-necked flask, the mixture was cooled to 3° C. (internal temperature), and 612 ml of tetrafluoroboric acid were added. 154 g of NaNO2 in 300 ml of water were then added dropwise over the course of 60 minutes. After 60 minutes, the solid was filtered off with suction and washed with a little cold 5% tetrafluoroboric acid, then with a little cold methanol and finally with a little cold diethyl ether. The yellow solid (497 g=90%) was dried overnight in an oil-pump vacuum.

Workup

  1. additionwere added
  2. filtrationthe solid was filtered off with suction
  3. washwashed with a little cold 5% tetrafluoroboric acid
  4. customThe yellow solid (497 g=90%) was dried overnight in an oil-pump vacuum

Sources & evidence

ORD record
ord-e51053d09f1b4274b143001d3f3e033a
Source dataset
uspto-grants-2003_10
Patent number
US06638646B2

Reaction notes

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