Sodium hydride → 1-Bromo-4-[(2,2-dimethoxyethyl)sulfanyl]benzene

HRID 2282081Notes

Reaction equation

HRID 2282081 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14]Br>C1COCC1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:14][CH:13]([O:16][CH3:17])[O:12][CH3:11])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 660494-BromothiophenolHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 141757601-Bromo-4-[(2,2-dimethoxyethyl)sulfanyl]benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (1.2 g, 20.5 mmol, 60% in mineral oil) was added to a dry THF (20 ml) solution of 4-bromobenzene thiol (3.0 g, 15.8 mmol) and reacted at room temperature for 10 minutes. Next, bromoacetaldehyde dimethyl acetal (2.8 mL, 23.7 mmol) was added to the mixture and reacted while being refluxed for two days.

Workup

  1. customreacted at room temperature for 10 minutes
  2. customreacted
  3. temperaturewhile being refluxed for two days

Sources & evidence

ORD record
ord-9bc42db7bd3749f1bf9b6d2e6ecfa9a9
Source dataset
uspto-grants-2015_09
Patent number
US09139774B2

Reaction notes

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