Hydrochloric Acid → 858680-24-7

HRID 735156Notes

Reaction equation

HRID 735156 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].Cl.N([O-])=O.[Na+].[I-:20].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C.O>[I:20][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 2826272-bromo-4-phenylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 68817951858680-24-7

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
15 °C

Procedure

A solution of 7.3 g (29.4 mmol) of 3-bromobiphenyl-4-ylamine in 120 mL of acetic acid is mixed with 6 mL of concentrated hydrochloric acid at ambient temperature, cooled to 15° C., and stirred for 30 minutes. A solution of 2 g (28.9 mmol) of sodium nitrite in 7 mL of water is slowly added dropwise to this reaction mixture at 15° C. and stirred for 30 minutes. Then at 5° C., a solution of 5.4 g (32.5 mmol) of potassium iodide in 28 mL of water is slowly added dropwise and the mixture is stirred. After 30 minutes, 2.95 g of sodium thiosulfate is added and the mixture is stirred for a further 30 minutes. Then the reaction mixture is evaporated down and combined with water/ethyl acetate. The aqueous phase is again extracted with ethyl acetate, the combined aqueous phases are extracted once with water and dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: petroleum ether). Yield: 6.6 g (85% of theory); C12H8BrI (M=359.00); calc.: molecular ion peak (M)+: 358/360 (Br); found: molecular ion peak (M)+: 358/360 (Br).

Workup

  1. stirringstirred for 30 minutes
  2. stirringthe mixture is stirred
  3. waitAfter 30 minutes
  4. stirringthe mixture is stirred for a further 30 minutes
  5. customThen the reaction mixture is evaporated down
  6. extractionThe aqueous phase is again extracted with ethyl acetate
  7. extractionthe combined aqueous phases are extracted once with water
  8. dry with materialdried over sodium sulfate
  9. customThe purification

Sources & evidence

ORD record
ord-a98ccf91f355463eabeb6886c0480318
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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