Bromine → HCID 59858673, compound

HRID 539491Notes

Reaction equation

HRID 539491 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][CH:10]=[O:11].O1CCOCC1.[Br:18]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Br:18][CH:9]([C:3]1[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[CH:10]=[O:11]

Participants

6

Reactant 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 312751,4-DioxaneHCID 53403477(2,6-Dimethylphenyl)acetaldehyde

Product 1

HCID 59858673HCID 59858673, compoundYield 103.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(2,6-dimethylphenyl)-acetaldehyde (4.4 g, 29.7 mmol) was dissolved in DCM (30 mL) and dioxane (50 mL) and a solution of bromine (1.7 mL, 32.7 mmol) in DCM (30 mL) was added dropwise at room temperature. Completion of reaction was determined by GC/MS. Upon completion, sodium thiosulfate aqueous solution was added and stirred for 10 minutes. The layers were separated, and washed twice with DCM (100 mL) and combined organics with 10% aqueous LiCl solution (100 mL). The organic layers were dried over sodium sulfate, filtered and the solvent was removed under reduced pressure to give 7 g (93%) of 2-bromo-2-(2,6-dimethylphenyl)acetaldehyde as an orange oil. NMR confirmed the product, which was used without further purification.

Workup

  1. customCompletion of reaction
  2. customThe layers were separated
  3. washwashed twice with DCM (100 mL)
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9fdcd1ed32b34b498330d173aa556f0b
Source dataset
uspto-grants-2014_10
Patent number
US08871361B2

Reaction notes

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