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

HRID 2226706Notes

Reaction equation

HRID 2226706 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-butylphenylethyne (Compound 24) starting with meta bromobenzoic acid (Compound 25), which is treated with trimethylaluminum in hexane to yield 3-tert-butyl bromobenzene (Compound 26). 3-Tert-butyl bromobenzene 26 is thereafter converted into the ethyne derivative 24 through the trimethylsilyl ethyne intermediate 27 in steps similar to the steps described in connection with Reaction Scheme 3.

Workup

  1. customReaction Scheme 4

Sources & evidence

ORD record
ord-db59335014fb4dd29890510db88e3f74
Source dataset
uspto-grants-1994_09
Patent number
US05349105

Reaction notes

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