Potassium Phosphate, Tribasic → 4-Phenyldibenzofuran

HRID 717994

Reaction equation

HRID 717994 reaction equation
I[C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O.C1(C)C=CC=CC=1>[C:15]1([C:2]2[C:7]3[O:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 4582574-IododibenzofuranHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 64257504-Phenyldibenzofuran

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4-iododibenzo[b,d]furan (4 g, 13.60 mmol), phenylboronic acid (1.99 g, 16.32 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.447 g, 1.08 mmol), Pd2(dba)2 (0.250 g, 0.272 mmol), K3PO4 (10.1 g, 47.6 mmol), 150 mL toluene and 15 mL water were charged in a 250 mL flask. The reaction mixture was degassed by bubbling N2 for 30 minutes and then heated to reflux under N2 overnight. The reaction was cooled to room temperature and the crude product was purified by silica gel column to yield 3.3 g (99%), which was confirmed by GC-MS.

Workup

  1. customThe reaction mixture was degassed
  2. customby bubbling N2 for 30 minutes
  3. temperatureheated
  4. temperatureto reflux under N2 overnight
  5. customthe crude product was purified by silica gel column
  6. customto yield 3.3 g (99%), which

Sources & evidence

ORD record
ord-373797317bbe4301a53ec9f78b8163fc
Source dataset
uspto-grants-2015_11
Patent number
US09193745B2

Linked notes

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