Sulfuric Acid → HCID 118598114, compound

HRID 63618Notes

Reaction equation

HRID 63618 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[Si]([C:21]#[N:22])(C)(C)C.[OH:23]S(O)(=O)=O>C1(C)C=CC=CC=1.O.CC(O)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:21]([NH2:22])=[O:23])=[CH:7][CH2:8][O:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 1118Sulfuric Acid2×HCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) ChlorideHCID 223357367-bromo-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 118598114HCID 118598114, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 7-bromochroman-4-one (2.0 g, 8.8 mmol) and AlCl3 (118 mg, 0.9 mmol) in toluene (10 mL) was added TMSCN (1.3 mL, 9.7 mmol). The solution was stirred at 40° C. for 1.5 h. The reaction was cooled to rt, and H2SO4 (1.0 mL) was added, followed by AcOH (13 mL) and more H2SO4 (4.3 mL). The reaction was heated to 130° C. and stirred for 6 h. The reaction was cooled, poured over H2O (100 mL) and filtered. The filter cake dissolved in THF (50 mL) and filtered. The combined organic solutions were concentrated to give 1.0 g (45%) of the crude title compound as an off-white solid. [M+H] calc'd for C10H8BrNO2, 254, 256. found 254, 256.

Workup

  1. temperatureThe reaction was cooled to rt
  2. temperatureThe reaction was heated to 130° C.
  3. stirringstirred for 6 h
  4. temperatureThe reaction was cooled
  5. filtrationfiltered
  6. dissolutionThe filter cake dissolved in THF (50 mL)
  7. filtrationfiltered
  8. concentrationThe combined organic solutions were concentrated

Sources & evidence

ORD record
ord-4c7efe1c71174b10acaa9f517e2027b1
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Reaction notes

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