Tetrabutylammonium Fluoride → 3-Bromo-4-ethynylbiphenyl

HRID 735157Notes

Reaction equation

HRID 735157 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:19][C:20]1[CH:21]=[C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:23]=[CH:24][C:25]=1[C:26]#[C:27][Si](C(C)(C)C)(C)C>C1COCC1>[Br:19][C:20]1[CH:21]=[C:22]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:23]=[CH:24][C:25]=1[C:26]#[CH:27]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68817863(3-Bromobiphenyl-4-ylethynyl)-tert-butyldimethylsilane

Product 1

HCID 860607363-Bromo-4-ethynylbiphenyl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.99 mL (1.99 mmol) of a 1M tetrabutylammonium fluoride solution in THF is added batchwise at 5° C. to a solution of 495 mg (1.33 mmol) of (3-bromobiphenyl-4-ylethynyl)-tert-butyldimethylsilane in 8 mL of anhydrous THF. The reaction mixture is stirred for another 30 minutes at ambient temperature and evaporated down. The residue is combined with diethyl ether and water and the organic phase is dried over sodium sulfate. Yield: 0.34 g (99% of theory); C14H9Br (M=257.12); calc.: molecular ion peak (M−H)−: 255/257 (Br); found: molecular ion peak (M−H)−: 255/257 (Br).

Workup

  1. customevaporated down
  2. dry with materialthe organic phase is dried over sodium sulfate

Sources & evidence

ORD record
ord-ce0087346a914ada91830205f2a9702d
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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