Triphenylphosphine → 3-Bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile

HRID 627854Notes

Reaction equation

HRID 627854 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].[S:11]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17]O)=[CH:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][S:11][CH:12]=1)[C:5]#[N:6]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 753413-Bromo-4-hydroxybenzonitrileHCID 83731Thiophene-3-ethanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 568341533-Bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-bromo-4-hydroxybenzonitrile (15.0 g) in THF (100 mL) was added 2-(3-thienyl)ethanol (7.94 mL) and triphenyl phosphine (19.84 g). The reaction was cooled to 0° C. and diethylazodicarboxylate (11.92 mL) was added dropwise. The reaction was stirred at room temperature for 16 h. The solvent was then reduced in vacuo and the residue redissolved in diethyl ether (100 mL) The mixture was stirred at 0° C. for 10 min and then filtered. The filtrate was washed with aqueous sodium carbonate solution (80 mL), 1 M aqueous hydrochloric acid (80 mL) and brine (80 mL), dried (MgSO4), reduced in vacuo and purified on silica to give 3-bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile.

Workup

  1. stirringwas stirred at 0° C. for 10 min
  2. filtrationfiltered
  3. washThe filtrate was washed with aqueous sodium carbonate solution (80 mL), 1 M aqueous hydrochloric acid (80 mL) and brine (80 mL)
  4. dry with materialdried (MgSO4)
  5. custompurified on silica

Sources & evidence

ORD record
ord-3fea7684612c4515854cce244bb049d8
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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