Sodium hydride → Bis(4-trifluoromethylthiobenzyl)ether

HRID 1358737

Reaction equation

HRID 1358737 reaction equation
[H-].[Na+].[F:3][C:4]([F:15])([F:14])[S:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=1.[F:16][C:17]([F:28])([F:27])[S:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1>C1COCC1>[F:15][C:4]([F:14])([F:3])[S:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][O:11][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([S:18][C:17]([F:28])([F:16])[F:27])=[CH:20][CH:21]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27778704-((Trifluoromethyl)thio)benzenemethanolHCID 27778824-(Trifluoromethylthio)benzyl bromide

Product 1

HCID 12112481Bis(4-trifluoromethylthiobenzyl)etherYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (65 mg 60% dispersion oil, 1.58 mmol) was added to a solution of 4-(trifluoromethylthio)benzyl alcohol (300 mg, 1.44 mmol) in THF (10 mL) at rt. After stirring for 10 min, to the mixture was added 4-(trifluoromethylthio)benzyl bromide (410 mg, 1.51 mmol), stirring was continued overnight. The reaction was quenched with saturated ammonium chloride solution, extracted with EtOAc, washed with water and dried to give 0.5 g (85%) of bis(4-trifluoromethylthiobenzyl) ether as a yellow oil. 1HNMR (360 MHz, DMSO-d6) δ 7.70 (d, J=8.1 Hz, 4H), 7.53 (d, J=8.1 Hz, 4H), 4.65 (s, 4H, CH2OCH2). MS-EI m/z 398 [M+].

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe reaction was quenched with saturated ammonium chloride solution
  4. extractionextracted with EtOAc
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-b6758ded59d74e05aee992c35e218b2b
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Linked notes

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