Reaction #53455

Reaction equation

1-benzhydryl-3-[(3-methoxyphenyl)(methylsulfonyl)methylene]azetidine

→

1-benzhydryl-3-[(3-hydroxyphenyl)(methylsulfonyl)methylene]azetidine

Yield 28.7%

Solvents

dichloromethane

dichloromethane

—

ice

Conditions

Workup

1. 1
   WashThe organic phase is washed with 3 times 50 cm3 of water
2. 2
   Dryingdried over magnesium sulfate
3. 3
   Concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
4. 4
   OtherThe residue is precipitated in 150 cm3 of isopropyl ether
5. 5
   workup.DISSOLUTIONdissolved in 50 cm3 of dichloromethane
6. 6
   WashThe organic phase is washed with 3 times 30 cm3 of a saturated aqueous solution of sodium bicarbonate
7. 7
   Otherdecanted off
8. 8
   Dryingdried over magnesium sulfate
9. 9
   Concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
10. 10
    OtherThe residue is precipitated in 80 cm3 of ethyl ether

Procedure

10 cm3 of a 1 M solution of boron tetrabromide in dichloromethane are added, with stirring, to a solution of 1.3 g of 1-benzhydryl-3-[(3-methoxyphenyl)(methylsulfonyl)methylene]azetidine in 100 cm3 of dichloromethane. The stirring is maintained for 16 hours at room temperature. The reaction medium is taken up in 100 cm3 of ice-cold water. The organic phase is washed with 3 times 50 cm3 of water, dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is precipitated in 150 cm3 of isopropyl ether and then dissolved in 50 cm3 of dichloromethane. The organic phase is washed with 3 times 30 cm3 of a saturated aqueous solution of sodium bicarbonate, decanted off, dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is precipitated in 80 cm3 of ethyl ether. 0.36 g of 1-benzhydryl-3-[(3-hydroxyphenyl)(methylsulfonyl)methylene]azetidine is obtained from a solid melting at 248° C. [NMR spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 2.95 (3H, s, SCH3), 3.80 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.75 (1H, s, NCH), 6.85 (3H, m, 3 CH arom.), 7.25 (3H, m, 3 CH arom.), 7.35 (4H, t, J=7 Hz, 4CH arom.), 7.50 (4H, d, J=7 Hz, 4CH arom.), 9.50 (1H, s, OH)].

Source