Triethyl phosphite → HCID 58750876, compound

HRID 2373506Notes

Reaction equation

HRID 2373506 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[P:17]([O:24]CC)([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>[Ni](Br)Br>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH:3][CH:4]=2)=[O:9])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 74951(4-Bromophenyl)(4-fluorophenyl)methanone2×

Product 1

HCID 58750876HCID 58750876, compound

Reagents, catalysts & solvents 1

HCID 278492Nickel(II) bromideCatalyst

Procedure

(4-Bromophenyl)(4′-fluorophenyl)methanone (formula 28) (400 g, 1.43 mol) from Example 4A and anhydrous nickel bromide (35 g, 0.16 mol) are heated to 160° C. under an atmosphere of nitrogen. A green-blue colored melt is obtained. Then triethyl phosphite (304 g, 1.83 mol) is added over a period of 1 hour while maintaining the temperature between 160 and 165° C. The mixture is stirred at this temperature for an additional hour. Distillation of the mixture gave a pale yellow oil, b.p. 187-188° C./10-2 mbar. The yield is 304-326 g (63-68%).

Workup

  1. customA green-blue colored melt is obtained
  2. temperaturewhile maintaining the temperature between 160 and 165° C
  3. distillationDistillation of the mixture
  4. customgave a pale yellow oil, b.p. 187-188° C./10-2 mbar

Sources & evidence

ORD record
ord-add68dc3548e4d9b9733307a55cab7f3
Source dataset
uspto-grants-2008_12
Patent number
US07459505B2

Reaction notes

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