Lithium Bromide → HCID 14468512, compound

HRID 1475392Notes

Reaction equation

HRID 1475392 reaction equation
[Li+].[Br-:2].Cl[CH2:4][C:5](=[CH2:15])[CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C1COCC1>[Br:2][CH2:4][C:5](=[CH2:15])[CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 82050Lithium BromideHCID 11171584Benzene, [[[2-(chloromethyl)-2-propenyl]oxy]methyl]-

Product 1

HCID 14468512HCID 14468512, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

LiBr (2.7 g, 31.6 mmol) was flame dried under vacuum and then cooled to room temperature. TBABr (255 mg, 0.79 mmol), (2-chloromethyl-allyloxymethyl)-benzene (3.1 g, 15.8 mmol) and THF (5 mL) were then added and the suspension was stirred at 60° C. for 2 h. The mixture was filtered through Celite and the solvent was removed in vacuo to give the title compound (3.4 g) as a colourless oil which was used in the next step without further purification. 1H NMR (CDCl3): 7.47-7.30 (5H, m), 5.47-5.33 (1H, m), 5.30 (1H, q), 4.56 (2H, s), 4.19 (2H, s), 4.08 (2H, s).

Workup

  1. customdried under vacuum
  2. filtrationThe mixture was filtered through Celite
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-eb8e2c9c17c2442ebde3e1497e8626e4
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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