Boron tribromide → 1-[Bis(4-chlorophenyl)methyl]-3-[(3-hydroxyphenyl)(methylsulfonyl)methylene]azetidine

HRID 25186Notes

Reaction equation

HRID 25186 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[N:9]2[CH2:12][C:11](=[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=3)[S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10]2)=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:9]2[CH2:12][C:11](=[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=3)[S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10]2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 102065291-[Bis(4-chlorophenyl)methyl]-3-[(3-methoxyphenyl)(methylsulfonyl)methylene]azetidine

Product 1

HCID 101839171-[Bis(4-chlorophenyl)methyl]-3-[(3-hydroxyphenyl)(methylsulfonyl)methylene]azetidineYield 2.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

On carrying out the operation according to the procedure of Example 32 starting with 4.8 g of 1-[bis(4-chlorophenyl)methyl]-3-[(3-methoxyphenyl)(methylsulfonyl)methylene]azetidine, 32 cm3 of a 1 M solution of boron tribromide in dichloromethane, the residue obtained is purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 3 cm, height 30 cm), at a nitrogen pressure of 0.5 bar with a mixture of dichloromethane and ethanol (98/2 by volume) as eluent and collecting 20 cm3 fractions. Fractions 16 to 17 are concentrated to dryness under reduced pressure (2.7 kPa). 0.1 g 1-[bis(4-chlorophenyl)methyl]-3-[(3-hydroxyphenyl)(methylsulfonyl)methylene]azetidine is obtained, after recrystallization from 5 cm3 of diethyl ether, in the form of a solid melting at 114° C. [NMR spectrum in DMSO-d6, T=300K, δ in ppm (250 MHz): 2.92 (3H, s, SCH3), 3.80 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.80 (1H, s, NCH), 6.80 (3H, m, 3CH arom.), 7.20 (1H, t, J=7 Hz, CH arom.), 7.37 (4H, t, J=7 Hz, 4CH arom.), 7.47 (4H, d, J=7 Hz, 4 CH arom.)].

Workup

  1. customthe residue obtained
  2. customis purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 3 cm, height 30 cm), at a nitrogen pressure of 0.5 bar with a mixture of dichloromethane and ethanol (98/2 by volume) as eluent
  3. customcollecting 20 cm3 fractions
  4. concentrationFractions 16 to 17 are concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-8fa8038a6c3042858af81c3549e0e101
Source dataset
uspto-grants-2005_02
Patent number
US06858603B2

Reaction notes

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