Bromotrimethylsilane → 2-Bromo-5-(4-fluorophenyl) tetrahydrofuran

HRID 1490250Notes

Reaction equation

HRID 1490250 reaction equation
[Si](O[CH:9]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[O:10]1)(C(C)(C)C)(C)C.C[Si]([Br:25])(C)C>C(Cl)Cl>[Br:25][CH:9]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[O:10]1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 541945292-(t-Butyldimethylsilyloxy)-5-(4-fluorophenyl) tetrahydrofuran

Product 1

HCID 536587122-Bromo-5-(4-fluorophenyl) tetrahydrofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

2-(t-Butyldimethylsilyloxy)-5-(4-fluorophenyl) tetrahydrofuran (202, 593 mg, 2.0 mmol) was mixed in 10 mL of dry methylene chloride (degassed by bubbling argon prior to use). This solution was cooled to -70° C. While stirring at the same temperature under dry argon, trimethylsilyl bromide (290 μL, 2.2 mmol) was added dropwise. The stirring was continued for an additional 1.5 h to produce 2-bromo-5-(4-fluorophenyl) tetrahydrofuran (203) which was not isolated and was used in subsequent chemistry without further purification (see below).

Workup

  1. customdegassed
  2. customby bubbling argon

Sources & evidence

ORD record
ord-70463ec8893e48bc929b79b55ab0937e
Source dataset
uspto-grants-1997_10
Patent number
US05681966

Reaction notes

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