Sodium hydride → 4-(Adamantan-1-ylmethoxy)-3-bromobenzonitrile

HRID 1849498Notes

Reaction equation

HRID 1849498 reaction equation
[C:1]12([CH2:11][OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].F[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=1[Br:24]>O1CCCC1>[C:1]12([CH2:11][O:12][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][C:17]=3[Br:24])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 1235793-Bromo-4-fluorobenzonitrile

Product 1

HCID 867028434-(Adamantan-1-ylmethoxy)-3-bromobenzonitrileYield 80.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of adamantan-1-ylmethanol (12.47 g, 75.00 mmol) in anhydrous tetrahydrofuran (100 mL) was added sodium hydride (60% w/w in mineral oil, 3.30 g, 82.50 mmol) at 0° C. The resulting mixture was stirred at ambient temperature for 2 h, followed by the addition of 4-fluoro-3-bromobenzonitrile (15.00 g, 75.00 mmol). Stirring was continued at ambient temperature for 17 h, cooled to 0° C. and quenched with saturated ammonium chloride solution (20 mL). The volatiles were removed by evaporation in vacuo. The residue was washed with water and diethyl ether to give the title compound as a pale yellow solid (21.00 g, 80%): 1H NMR (300 MHz, CDCl3) δ 7.80-7.78 (m, 1H), 7.56-7.51 (m, 1H), 6.88-6.84 (m, 1H), 3.57 (s, 3H), 2.02 (br s, 3H), 1.73-1.55 (m, 12H).

Workup

  1. stirringStirring
  2. waitwas continued at ambient temperature for 17 h
  3. temperaturecooled to 0° C.
  4. customquenched with saturated ammonium chloride solution (20 mL)
  5. customThe volatiles were removed by evaporation in vacuo
  6. washThe residue was washed with water and diethyl ether

Sources & evidence

ORD record
ord-252faa6194fb448eba9b0633abf9ab11
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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