Thionyl Chloride → HCID 59325362, compound

HRID 2277754Notes

Reaction equation

HRID 2277754 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:11]O)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.S(Cl)([Cl:15])=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN1C(=O)CCC1>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH2:11][Cl:15])[CH:3]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 14866972(3-Bromo-5-nitrophenyl)methanol

Product 1

HCID 59325362HCID 59325362, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirring solution of (3-bromo-5-nitrophenyl)methanol (5.00 g; 21.5 mmol; Biogene Organics Inc) in DCM (65 mL) and NMP (9 mL) at RT was added dropwise thionylchloride (3.9 mL; 53.9 mmol). The mixture was allowed to react at RT overnight. Then, the mixture was poured into aqueous sodium bicarbonate solution/saturated aqueous sodium chloride solution/ice. The batch was stirred for one hour before it was extracted with ethyl acetate (2×). The combined organic phases were filtered using a Whatman filter and concentrated to give crude 1-bromo-3-(chloromethyl)-5-nitrobenzene, that was used without further purification.

Workup

  1. customto react at RT overnight
  2. extractionwas extracted with ethyl acetate (2×)
  3. filtrationThe combined organic phases were filtered
  4. filtrationfilter
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-871deeb2e689497f9fc8afbf51fe9093
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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