Dichloromethane → 8-Acetyl-6-bromo-2,2,4,4-tetramethyl chroman

HRID 2377330Notes

Reaction equation

HRID 2377330 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]2([CH3:15])[CH3:14].ClCCl.[Cl-].[Al+3].[Cl-].[Cl-].[C:23](Cl)(=[O:25])[CH3:24]>O>[C:23]([C:10]1[CH:11]=[C:2]([Br:1])[CH:3]=[C:4]2[C:9]=1[O:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]2([CH3:15])[CH3:14])(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 121370056-Bromo-2,2,4,4-tetramethylchroman

Product 1

HCID 211072398-Acetyl-6-bromo-2,2,4,4-tetramethyl chromanYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred, cooled (−78° C.) solution of 6-bromo-2,2,4,4-tetramethyl chroman (1 g, 3.72 mol) in anhydrous dichloromethane (10 mol) was treated with aluminum chloride (0.8 g, 6.8 mol) followed by acetyl chloride (0.4 mol, 6.08 mol). After 10 minutes, the reaction mixture was diluted with water and extracted with diethyl ether. The organic phase was washed with water, and dried over anhydrous sodium sulfate, filtered and evaporated to a residue that was subjected to flash column chromatography on silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent to afford the title compound as a solid (0.78 g, 67%).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated to a residue that

Sources & evidence

ORD record
ord-73add12814054bf19e319dadea78c7fc
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

Loading…