4-Bromobenzoyl chloride → HCID 21182619, compound

HRID 1387099Notes

Reaction equation

HRID 1387099 reaction equation
[S:1]1[C:5]([C:6]2[CH:19]=[CH:18][C:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:8][CH:7]=2)=[CH:4][C:3]2[CH:20]=[CH:21][CH:22]=[CH:23][C:2]1=2.[Br:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1.C([O-])(O)=O.[Na+]>ClCCl.Cl[Ti](Cl)(Cl)Cl>[N:13]1([CH2:12][CH2:11][O:10][C:9]2[CH:18]=[CH:19][C:6]([C:5]3[S:1][C:2]4[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=4[C:4]=3[C:29]([C:28]3[CH:32]=[CH:33][C:25]([Br:24])=[CH:26][CH:27]=3)=[O:30])=[CH:7][CH:8]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 685154-Bromobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 106637082-[4-[2-(1-Pyrrolidinyl)ethoxy)phenyl]benzo[b]thiophene

Product 1

HCID 21182619HCID 21182619, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2-[4-(benzo[b]thiophen-2-yl)phenoxy]ethyl]pyrrolidine (650 mg, 2.0 mmol) and 4-bromobenzoyl chloride (657 mg, 1.5 equiv) in dichloromethane (25 mL) at 0° C. in dark was added TiCl4 (1.0 mL, neat) slowly under argon. The resulting mixture was stirred at ambient temperature for 4 h before being transferred carefully to a stirring solution of saturated aqueous NaHCO3 (100 mL). After stirring for 30 min, the mixture was extracted with CH2Cl2 (3×100 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Chromatography with Et3N:MeOH:EtOAc (4:4:92) afforded the product (940 mg, 92%).

Workup

  1. stirringAfter stirring for 30 min
  2. extractionthe mixture was extracted with CH2Cl2 (3×100 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac555f8f6a0a4f57bb7bb03d9571165e
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

Loading…