Boron tribromide → HCID 22565391, compound

HRID 1058785Notes

Reaction equation

HRID 1058785 reaction equation
[CH:1]([N:14]1[CH2:17][C:16](=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29]C)[S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[CH:1]([N:14]1[CH2:17][C:16](=[C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22565390HCID 22565390, compound

Product 1

HCID 22565391HCID 22565391, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

On carrying out the operation according to the procedure of Example 32 starting with 1.4 g of 1-benzhydryl-3-[(2-methoxyphenyl)(methylsulfonyl)methylene]azetidine, 10 cm3 of a 1 M solution of boron tribromide and 100 cm3 of dichloromethane, the residue obtained is purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 4 cm, height 30 cm) at a nitrogen pressure of 0.5 bar with dichloromethane as eluent and collecting 40 cm3 fractions. Fractions 15 to 34 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is crystallized from 40 cm3 of ethyl ether. 0.7 g of 1-benzhydryl-3-[(2-hydroxyphenyl)(methylsulfonyl)methylene]azetidine is obtained melting at 196° C. [NMR spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 3.00 (3H, s, SCH3), 3.60 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.75 (1H, s, NCH), 6.85 (1H, t, J=7 Hz, CH arom.), 6.90 (1H, d, J=7 Hz, CH arom.), 7.20 (4H, m, 4CH arom.), 7.30 (4H, t, J=7 Hz, 4CH arom.), 7.48 (4H, d, J=7 Hz, 4CH arom.), 9.90 (1H, s, OH)].

Workup

  1. customthe residue obtained
  2. customis purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 4 cm, height 30 cm) at a nitrogen pressure of 0.5 bar with dichloromethane as eluent
  3. customcollecting 40 cm3 fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe solid obtained
  6. customis crystallized from 40 cm3 of ethyl ether

Sources & evidence

ORD record
ord-ea29e04d27e84344bd888296a2e5b8cf
Source dataset
uspto-grants-2003_02
Patent number
US06518264B2

Reaction notes

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