Hydrochloric Acid → HCID 18445393, compound

HRID 460306Notes

Reaction equation

HRID 460306 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]2[CH:7]=[C:8]([C:11](=[O:13])[CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.[Al+3].[Cl-].[Cl-].[Cl-].[Br:19]Br.Cl>ClCCl>[Br:19][C:10]1[C:5]2[O:4][CH2:3][C:2]([CH3:14])([CH3:1])[C:6]=2[CH:7]=[C:8]([C:11](=[O:13])[CH3:12])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 10774045HCID 10774045, compound

Product 1

HCID 18445393HCID 18445393, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(3,3-dimethyl-2,3-dihydro-benzofuran5-yl)-ethanone (1.69 g, 8.88 mmol) in dichloromethane (25 mL) was slowly added a suspension of AlCl3 (2.96 g, 22.2 mmol) in dichloromethane (30 mL). Bromine (1.61 g, 10.7 mmol) was added dropwise and the mixture was stirred at room temperature for 6 hours then cooled to 0° C. and aqueous HCl (1N) was added and the mixture extracted with dichloromethane, washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane: EtOAc/10:1 to 2:1) to give 1.94 g 1-(7-Bromo-3,3-dimethyl-2,3-dihydro-benzofuran5-yl)-ethanone (81%). 1H NMR (300 MHz, CDCl3, ppm): δ: 1.39 (s, 6H), 2.56 (s, 3H), 4.37 (s, 2H), 7.69 (d, J=1.76 Hz, 1H), 7.95 (d, J=1.76 Hz, 1H).

Workup

  1. temperaturethen cooled to 0° C.
  2. extractionthe mixture extracted with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane: EtOAc/10:1 to 2:1)

Sources & evidence

ORD record
ord-1daddc323801469bac9e88209e448a0e
Source dataset
uspto-grants-2007_03
Patent number
US07196108B2

Reaction notes

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