Bromobenzene → 1-Phenylnaphthalene

HRID 1876933Notes

Reaction equation

HRID 1876933 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(B(O)O)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>>[C:2]1([C:16]2[C:17]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:13]=[CH:14][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7961BromobenzeneHCID 8471TriethylamineHCID 2545321-Naphthaleneboronic acid

Product 1

HCID 117951-PhenylnaphthaleneYield 98%

Procedure

A solution of bromobenzene (1 mmol), of 1-naphthylboronic acid (1.2 mmol), of PdBr2 (2.5 mol %), and of triethylamine (2 mmol) in N,N′-butylmethylimidazolium methyl H-phosphonate of (1 g) is brought to 100° C. under stirring for 24 hrs. Extraction with hexane (3×5 mL) gives a white and sublimable solid (Mp 112-113° C.), (m=0.2 g; yield=98%).

Workup

  1. customis brought to 100° C.
  2. extractionExtraction with hexane (3×5 mL)

Sources & evidence

ORD record
ord-33e88d49357a4d9d976212e5ab7c7f35
Source dataset
uspto-grants-2012_11
Patent number
US08309736B2

Reaction notes

Loading…