Methanol → HCID 10689226, compound

HRID 1386983Notes

Reaction equation

HRID 1386983 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[C:10]=2[S:18][C:19]2[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.CO>ClC(Cl)C.C(Cl)(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[C:10]=2[S:18][C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 10714689HCID 10714689, compound

Product 1

HCID 10689226HCID 10689226, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 0.82 g (2.2 mmol) of methyl 4-[[2-(4-methoxyphenyl)benzo[b]thiophen-3-yl]thio]phenyl ether (Part B) in 50 mL of dichloroethane was treated with 1.2 mL (3.3 g; 13 mmol) of BBr3 at 0° C. for 5 h. The reaction was quenched by the careful addition of 15 mL of MeOH. Evaporation of the solvent in vacuo gave a residue which was subjected to flash chromatography (SiO2; 1% MeOH in CHCl3) to afford 0.47 g of the desired product as a solid.

Workup

  1. customThe reaction was quenched by the careful addition of 15 mL of MeOH
  2. customEvaporation of the solvent in vacuo
  3. customgave a residue which

Sources & evidence

ORD record
ord-94347ad530a343bc9539fa66f4629333
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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