1-Bromo-4-fluorobenzene → HCID 131714089, compound

HRID 2413296Notes

Reaction equation

HRID 2413296 reaction equation
[C:1]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][C:4]([Si:7]([CH2:13][Cl:14])([CH3:12])OC(C)C)=[CH:3][CH:2]=1.Br[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1.C([Li])CCC>O1CCCC1.CCCCCC>[C:1]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:2]=[CH:3][C:4]([SiH:7]([CH2:13][Cl:14])[CH2:12][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 99931-Bromo-4-fluorobenzeneHCID 13392401HCID 13392401, compoundHCID 178418339Butyllithium

Product 1

HCID 131714089HCID 131714089, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 10.0 g (32.8 mmol) of (1,1'-biphenyl-4-yl)(chloromethyl)methyl(2-propoxy)silane and 3.6 ml (32.8 mmol) of 4-bromofluorobenzene in 30 ml of dry tetrahydrofuran was cooled to -60° under nitrogen and stirred while 20.5 ml (32.8 mmol) of 1.6 molar n-butyllithium in hexane was added at a rate that held the mixture below 50°. After stirring at -70° for another 30 minutes, the solution was allowed to warm to room temperature and was worked up as in Example 8. The resulting crude product was subjected to distillation at 130°-150° (0.2 mm) to remove unreacted starting material, leaving the title compound as an oil: nD23 1.5128; nmr (CDCl3): 0.7 (3H, s), 3.1 (2H, s), 7.1 (2H, t), 7.2-7.8 (11H, m).

Workup

  1. additionwas added at a rate that
  2. customthe mixture below 50°
  3. distillationThe resulting crude product was subjected to distillation at 130°-150° (0.2 mm)
  4. customto remove unreacted

Sources & evidence

ORD record
ord-6adb738cb92249ec81d90e9632b9ac10
Source dataset
uspto-grants-1985_01
Patent number
US04496551

Reaction notes

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