Triethylamine → 1-(Bromomethyl)-3-[[3-(hexadecyloxy)-2-methoxypropoxy]methyl]benzene

HRID 2254067Notes

Reaction equation

HRID 2254067 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([O:31][CH3:32])[CH2:20][O:21][CH2:22][C:23]1[CH:24]=[C:25]([CH2:29]O)[CH:26]=[CH:27][CH:28]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].S(Cl)(C)(=O)=O.C(N(CC)CC)C.[Br-:45].[Li+]>O1CCCC1.CCOCC.O>[Br:45][CH2:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([CH2:22][O:21][CH2:20][CH:19]([O:31][CH3:32])[CH2:18][O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:24]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 82050Lithium BromideHCID 199395543-[[3-(Hexadecyloxy)-2-methoxypropoxy]methyl]benzenemethanol

Product 1

HCID 199395571-(Bromomethyl)-3-[[3-(hexadecyloxy)-2-methoxypropoxy]methyl]benzene

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4 g of 3-[[3-(hexadecyloxy)-2-methoxypropoxy]methyl]benzenemethanol and 3.05 g of mesyl chloride in 40 ml of tetrahydrofuran at 0° C. was added over 20 minutes a solution of 2.69 g of triethylamine in 10 ml of tetrahydrofuran. A 7.71 g portion of lithium bromide was added and the mixture was stirred at room temperature for 2 hours. The solution was diluted with ether, poured into water, and extracted with ethanol. The extract was washed with saturated sodium bicarbonate solution, dried and evaporated, giving the desired compound as an oil.

Workup

  1. extractionextracted with ethanol
  2. washThe extract was washed with saturated sodium bicarbonate solution
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-06a1b8162aa8435780ca2a2a25c1bd99
Source dataset
uspto-grants-1993_08
Patent number
US05234918

Reaction notes

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