Dichloromethane → 2-Bromo-3-(3,4-dichloro-phenyl)-propionaldehyde

HRID 1971831Notes

Reaction equation

HRID 1971831 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH:11]=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(Cl)Cl.C[Si]([Br:20])(C)C.BrBr>O.O1CCOCC1>[Br:20][CH:10]([CH2:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH:11]=[O:12]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24408BromineHCID 76113BromotrimethylsilaneHCID 234995723-(3,4-Dichlorophenyl)propanal

Product 1

HCID 581268402-Bromo-3-(3,4-dichloro-phenyl)-propionaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product of example 37 (10 mmol, 2.0 g) in a mixed solvent of DCM (40 ml) with dioxane (4.0 ml) was added TMSBr (15 mmol, 2.3 g) at room temperature. After the mixture was kept at 25° C. for one hour, bromine (1.6 g, 10.0 mmol) was added. Another one hour later, the mixture was poured into water (50 ml) and extracted with DCM three times. The combined organic layers were washed with brine, dried and evaporated into dryness to give the crude title product, which was used directly in the next step reaction.

Workup

  1. extractionextracted with DCM three times
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. customevaporated into dryness

Sources & evidence

ORD record
ord-35dcfee7547d485687e67748015325b2
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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