Hydrochloric Acid → 1-(7-Bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-one

HRID 460286Notes

Reaction equation

HRID 460286 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][C:6]1([CH3:20])[C:10]2[CH:11]=[C:12]([C:15](=[O:19])[CH:16]([CH3:18])[CH3:17])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7]1.[Br:21]Br.Cl>ClCCl>[Br:21][C:14]1[C:9]2[O:8][CH2:7][C:6]([CH3:5])([CH3:20])[C:10]=2[CH:11]=[C:12]([C:15](=[O:19])[CH:16]([CH3:17])[CH3:18])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 184453861-(3,3-Dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-one

Product 1

HCID 184453921-(7-Bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-oneYield 107.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of AlCl3 (1.5 g, 11.32 mmol) in dry dichloromethane (30 mL) was added dropwise at room temperature 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-one (989 mg, 4.52 mmol) in dichloromethane (15 mL) followed by bromine (0.28 mL, 5.43 mmol) and the reaction stirred for 6 hours. 1N HCl was added slowly and the layers separated. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed successively with aq. K2CO3, water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated to give 1.44 g of 1-(7-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-one (91%). 1H NMR (300 MHz; CDCl3): δ 1.21 (d, J=6.9 Hz, 6H), 1.39 (s, 6H), 3.47 (m, 1H), 4.43 (s, 2H), 7.70 (s, 1H), 7.95 (s, 1H). e. 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-one.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. washThe combined organic layers were washed successively with aq. K2CO3, water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-809e3f34adc74e2b9600b592de8e632b
Source dataset
uspto-grants-2007_03
Patent number
US07196108B2

Reaction notes

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