Boron tribromide → HCID 86583544, compound

HRID 1841738Notes

Reaction equation

HRID 1841738 reaction equation
B(Br)(Br)Br.[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:20]2[CH:25]=[CH:24][C:23]([O:26]C)=[C:22]([S:28][CH3:29])[CH:21]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=1)#[N:6]>C(Cl)Cl>[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([S:28][CH3:29])[CH:21]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=1)#[N:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86583545HCID 86583545, compound

Product 1

HCID 86583544HCID 86583544, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 1M solution of BBr3 in CH2Cl2 (4.5 ml, 4.5 mmol) was added at −78° C. to a solution of the ethyl (RS)-(4-cyano-phenylamino)-(4-methoxy-3-methylsulphanyl-phenyl)-acetate (320 mg, 0.899 mmol) obtained in Example 167.2 in CH2Cl2 (10 ml). The mixture was stirred at −78° C. for 5 min., at 0° C. for 30 min. and at room temperature for 2 h. Ice-water was added and the mixture was stirred for 10 min. The mixture was extracted with CH2Cl2. The organic phase was dried, filtered and concentrated. The residue was purified by chromatography (SiO2, hexane/EtOAc 2:1). Ethyl (RS)-(4-cyano-phenylamino)-(4-hydroxy-3-methylsulphanyl-phenyl)-acetate was obtained as a colorless oil (198 mg, 64%); MS: 343 ([M+H]+).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. extractionThe mixture was extracted with CH2Cl2
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (SiO2, hexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-465ca6d049104f90bf1d677179f7c981
Source dataset
uspto-grants-2004_01
Patent number
US06683215B2

Reaction notes

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