Sulfuric Acid → 6-chloro-5-methoxy-2,3-dihydro-1H-inden-1-one

Temperature

100 °C

To a solution of 1-chloro-2-methoxybenzene (12.8 mL, 100 mmol) and 3-chloropropanoyl chloride (10.5 mL, 110 mmol) in CH2Cl2 (100 mL) at 0° C. was added AlCl3 (14.6 g, 110 mmol) portionwise during about 1 minute. After 30 minutes, sulfuric acid (300 mL) was poured slowly into the reaction mixture during about 3 minutes. The CH2Cl2 was removed by rotary evaporation under reduced pressure and the viscous residue was stirred at 100° C. for 2 hours. After cooling to −50° C., the viscous reaction mixture was poured cautiously onto 1.5 L of ice and allowed to stand overnight. The mixture was filtered and the cake of crude product was washed with water. The crude product was dissolved in 500 mL of 2% MeOH in CH2Cl2, dried over a mixture of Na2CO3 (˜10 g) and Na2SO4 (˜20 g), filtered and concentrated under vacuum to give 6-chloro-5-methoxyindan-1-one as an off-white solid.

1. customThe CH2Cl2 was removed by rotary evaporation under reduced pressure
2. temperatureAfter cooling to −50° C.
3. additionthe viscous reaction mixture was poured cautiously onto 1.5 L of ice
4. waitto stand overnight
5. filtrationThe mixture was filtered
6. washthe cake of crude product was washed with water
7. dissolutionThe crude product was dissolved in 500 mL of 2% MeOH in CH2Cl2
8. dry with materialdried over a mixture of Na2CO3 (˜10 g) and Na2SO4 (˜20 g)
9. filtrationfiltered
10. concentrationconcentrated under vacuum

ORD record

ord-c023cb2d5cb641b2a9b46967ad6fd5f6

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923568B2