Chlorotrimethylsilane → HCID 59383072, compound

HRID 2355432Notes

Reaction equation

HRID 2355432 reaction equation
[Br:1][C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl[Si:12]([CH3:15])([CH3:14])[CH3:13].[Li+].CC([N-]C(C)C)C.C1COCC1.CCCCCCC>C1COCC1.CCOCC.Cl>[Br:1][C:2]1[C:7]2[CH:8]=[C:9]([Si:12]([CH3:15])([CH3:14])[CH3:13])[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 2724682Lithium diisopropylamideHCID 120942084-Bromobenzo[b]thiopheneHCID 21263495Tetrahydrofuran heptane

Product 1

HCID 59383072HCID 59383072, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

A stirred solution of ˜80% pure 4-bromobenzothiophene (580 mg, 2.7 mmol) and chlorotrimethylsilane (0.70 mL, 5.4 mmol) in dry THF (10 mL) was cooled to −70° C. and 2 M LDA in 1:1 THF/heptane (1.35 mL, 5.4 mmol) was added dropwise over 2 min. The mixture was stirred at −70° C. for 1.5 h and diluted with ether (80 mL) and 5% aq HCl (20 mL). The organic layer was separated, washed with sat'd aq NaHCO3 (20 mL) and dried over MgSO4. Removal of the solvent left 4-bromo-2-(trimethylsilyl)benzothiophene (740 mg, 95%) as an amber oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with sat'd aq NaHCO3 (20 mL)
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent
  5. waitleft 4-bromo-2-(trimethylsilyl)benzothiophene (740 mg, 95%) as an amber oil

Sources & evidence

ORD record
ord-b207a1bed93c40cbadfb68ab494c0cd9
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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