Dimethylformamide → 2-(1-Adamantyl)-4-bromo-1-decyloxybenzene

HRID 2165523

Reaction equation

HRID 2165523 reaction equation
[H-].[Na+].[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[OH:20])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.I[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].CN(C=O)C>C1COCC1.O>[C:3]12([C:13]3[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=3[O:20][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:4][CH:5]3[CH2:11][CH:9]([CH2:8][CH:7]([CH2:6]3)[CH2:12]1)[CH2:10]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 163141-IododecaneHCID 24758Sodium hydrideHCID 46704942-(1-Adamantyl)-4-bromophenol

Product 1

HCID 136335522-(1-Adamantyl)-4-bromo-1-decyloxybenzeneYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (80% in oil, 3.2 g, 104 mmol) in 100 ml of THF, there is slowly added a solution of 2-(1-adamantyl)-4-bromophenol (29 g, 95 mmol) in 200 ml of THF. The mixture is stirred until the evolution of gas ceases at which point 27.8 g (23 ml, 104 mmol) of 1-iododecane and 100 ml of DMF are added. The mixture is stirred for 12 hours at ambient temperature, poured into water, extracted with ether, dried and the solvents evaporated. The resulting residue is purified by passage through a silica column (eluant: heptane), yielding 40.7 g (96%) of 2-(1-adamantyl)-4-bromo-1-decyloxybenzene. Melting point: 69°-70° C.

Workup

  1. additionare added
  2. extractionextracted with ether
  3. customdried
  4. customthe solvents evaporated
  5. customThe resulting residue is purified by passage through a silica column (eluant: heptane)

Sources & evidence

ORD record
ord-8406e83a8e63460ca8f9dd66da5ab0ff
Source dataset
uspto-grants-1990_07
Patent number
US04940696

Linked notes

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