2-Bromotoluene → Biphenyl

HRID 1353974Notes

Reaction equation

HRID 1353974 reaction equation
B(O)O.Br[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:6]1([C:11]2[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:5]=1

Participants

4

Reactant 2

HCID 72362-BromotolueneHCID 61668Boronic Acid

Product 1

HCID 7095Biphenyl

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

Cyclization substrate 5 is synthesized in FIG. 1. The Suzuki reaction is iterated, first by coupling 1,3-dimethoxyphen-2-yl boronic acid with 2-bromotoluene with tetrakis(triphenylphosphine) palladium catalysis to give biphenyl compound 1. Regioselective bromination of 1 gave 2, followed by Suzuki reaction with pyridine-3-boronic acid under palladium catalysis to yield 3. Demethylation of 3 with hydrobromic acid and acetic acid gave 4, followed by Friedel-Crafts acylation with 2,5-dichlorotrimellitic anhydride to yield 5.

Workup

  1. customCyclization substrate 5 is synthesized in FIG. 1
  2. customThe Suzuki reaction

Sources & evidence

ORD record
ord-f424cb1166df4f0fba75b19f91deb8c4
Source dataset
uspto-grants-2007_05
Patent number
USRE039663E1

Reaction notes

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