3-Bromobenzoic acid → 1-Bromo-3-tert-butylbenzene

HRID 1681950Notes

Reaction equation

HRID 1681950 reaction equation
[C:1]([C:5]1[CH:6]=[C:7](C#C)[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br:13]C1C=C(C=CC=1)C(O)=O.C[Al](C)C>CCCCCC>[C:1]([C:5]1[CH:6]=[C:7]([Br:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 114563-Bromobenzoic acid2×HCID 149896671-(tert-Butyl)-3-ethynylbenzene2×HCID 16682925Trimethylaluminum

Product 1

HCID 3437981-Bromo-3-tert-butylbenzene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Reaction Scheme 4 discloses a specific synthetic route to 3-tert-butylphenyl ethyne (Compound 22) starting with meta bromobenzoic acid (Compound 23), which is treated with trimethylaluminum in hexane to yield 3-tert-butyl bromobenzene (Compound 24). 3-Tert-butyl bromobenzene 24 is thereafter converted into the ethyne derivative 22 through the trimethylsily ethyne intermediate 25 in steps similar to the steps described in connection with Reaction Scheme 3.

Workup

  1. customReaction Scheme 4

Sources & evidence

ORD record
ord-e1b4172a8de94ddbb689889bd65e14bb
Source dataset
uspto-grants-1992_12
Patent number
US05175185

Reaction notes

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