Benzyl Bromide → HCID 74057329, compound

HRID 1836469Notes

Reaction equation

HRID 1836469 reaction equation
[H-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH:15]=[N:16][OH:17]>CCCCCC.O1CCCC1.ClCCl>[CH2:3]([O:17][N:16]=[CH:15][C:14]1[CH:18]=[CH:19][C:20]([Cl:21])=[C:12]([Cl:11])[CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 2207415331-92-0

Product 1

HCID 74057329HCID 74057329, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
22 °C

Procedure

Sodium hydride (1.05 g of 60% suspension in mineral oil, 0.63 g, 26.3 mmol) was washed with hexane, suspended in tetrahydrofuran (10 ml) and then treated with benzyl bromide (2.7 ml, 22.8 mmol) A solution of the above oxime in tetrahydrofuran (10 ml) was then added dropwise and the resulting mixture was stirred at 22° C. for 18 h. The reaction mixture was then diluted with dichloromethane, washed with water, brine and dried. Evaporation of the solvent and chromatography of the residue on silica gel (elution hexane-toluene, 8:2 to 1:1) gave 4.30 g (67% yield) of the title oxime ether as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 5.12 (2H, s, OCH2), 7.3-7.44 (7H, m, aromatics), 7.68 (1H, d, aromatic), 8.04 (1H, s, CH).

Workup

  1. additionwas then added dropwise
  2. washwashed with water, brine
  3. customdried
  4. customEvaporation of the solvent and chromatography of the residue on silica gel (elution hexane-toluene, 8:2 to 1:1)

Sources & evidence

ORD record
ord-f62080dea45847469f01ccb40a461a2b
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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