1,2-Dibromoethane → HCID 69289142, compound

HRID 899079Notes

Reaction equation

HRID 899079 reaction equation
[Mg].BrCCBr.Cl[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15].[CH2:16]([N:23]1[CH2:28][CH2:27][O:26][CH:25]([C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:30])[CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(OCC)C>[CH2:16]([N:23]1[CH2:28][CH2:27][O:26][CH:25]([C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([OH:30])[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 814952-(Chloromethyl)anisoleHCID 5462224Magnesium2×HCID 179717622-Benzoyl-4-benzylmorpholine

Product 1

HCID 69289142HCID 69289142, compoundYield 122%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
15 °C

Procedure

Solid magnesium turnings (9.5 g, 28 equiv.) under nitrogen atmosphere at room temperature were stirred vigorously with a magnetic stirring bar overnight. The magnesium was then covered with dry diethyl ether and to the suspension was added 1,2-dibromoethane (50 μL). A cold bath was then applied followed by dropwise addition of 1-chloromethyl-2-methoxy-benzene (18.18 g, 5 equiv. available from Aldrich Chemical Company) in diethyl ether (71 mL) which maintained the temperature at up to 15° C. The resulting black suspension was stirred at room temperature for 30 minutes and cooled down at −20° C. A solution of (4-Benzyl-morpholin-2-yl)-phenyl-methanone (4 g, 1 equiv.) in diethyl ether (50 mL) was then added dropwise via canula. The reaction mixture was left to warm to room temperature over two hours and then quenched by addition of aqueous saturated solution of NaHCO3 (50 mL). The aqueous solution was extracted with diethyl ether, the organic phase dried with MgSO4, evaporated in vacuo to give 7 g of a yellow amorphous solid. The compound was taken without further purification in the next step. FIA [M+H]+=404.

Workup

  1. temperaturecooled down at −20° C
  2. waitThe reaction mixture was left
  3. temperatureto warm to room temperature over two hours
  4. customquenched by addition of aqueous saturated solution of NaHCO3 (50 mL)
  5. extractionThe aqueous solution was extracted with diethyl ether
  6. dry with materialthe organic phase dried with MgSO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-c4b0ec9856674e4c927b7e5a47d45231
Source dataset
uspto-grants-2008_04
Patent number
US07354920B2

Reaction notes

Loading…