4-Bromoanisole → HCID 18322216, compound

HRID 1698842Notes

Reaction equation

HRID 1698842 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.BrBr.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][N:23]2[C:27](=[O:28])[C:26]3=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]3[C:24]2=[O:33])[CH:18]=[CH:19][CH:20]=1.C(=O)(O)[O-].[Na+]>C(OCC)C>[OH:33][C:24]1([C:3]2[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=2)[C:25]2[C:26](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](=[O:28])[N:23]1[CH2:22][CH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[CH:16]=1

Participants

7

Reactant 5

HCID 77304-BromoanisoleHCID 24408BromineHCID 516892Sodium BicarbonateHCID 5462224Magnesium2×HCID 18322222HCID 18322222, compound

Product 1

HCID 18322216HCID 18322216, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

104 mg (4.28 mmol) of magnesium turnings in 10 ml of absolute diethyl ether were admixed with 0.79 g (4.27 mmol) of 4-bromoanisole. The reaction was started by addition of a drop of bromine. After about 2 h, the magnesium had completely dissolved. The mixture was cooled to 0° C. and 0.3 g (1.07 mmol) of N-(2-(3-methoxyphenyl)ethyl)phthalimide was added. The reaction mixture was allowed to warm to room temperature and, after 2 h, admixed with 5 ml of saturated sodium bicarbonate solution. The aqueous phase was extracted twice with diethyl ether. The combined organic phases were dried and evaporated to dryness using a rotary evaporator. The resulting oil was purified by chromatography. Elution was carried out using a dichloromethanelmethanol gradient (0 to 2% methanol). The product, obtained as a colorless oils was foamed by coevaporation with diethyl ether. Yield: 0.32 g. M.p.: 119° C.

Workup

  1. temperatureto warm to room temperature and, after 2 h
  2. extractionThe aqueous phase was extracted twice with diethyl ether
  3. customThe combined organic phases were dried
  4. customevaporated to dryness
  5. customa rotary evaporator
  6. customThe resulting oil was purified by chromatography
  7. washElution
  8. customThe product, obtained as a colorless oils

Sources & evidence

ORD record
ord-8cd09ef543d44041a12c31402977fda8
Source dataset
uspto-grants-2002_02
Patent number
US06344468B1

Reaction notes

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