p-Bromochlorobenzene → HCID 131714090, compound

HRID 1980507Notes

Reaction equation

HRID 1980507 reaction equation
[Cl:1][CH2:2][SiH2:3][CH:4](Cl)Cl.Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14].CCCCCC.C([Li])CCC.Br[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1.C([Li])CCC>O1CCCC1.C(OCC)(=O)C>[Cl:1][CH2:2][SiH:3]([C:31]1[CH:32]=[CH:27][CH:28]=[CH:29][C:30]=1[Cl:33])[CH2:4][C:12]1[CH:11]=[CH:10][C:9]([Cl:14])=[CH:8][CH:13]=1

Participants

8

Reactant 5

HCID 7806p-BromochlorobenzeneHCID 127541-Bromo-2-chlorobenzeneHCID 57370169HCID 57370169, compoundHCID 178418244HCID 178418244, compoundHCID 178418339Butyllithium

Product 1

HCID 131714090HCID 131714090, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6.3 ml (8.2 g, 0.05 mol) of chloromethyl(dichloro)methylsilane and 8.1 g (0.05 mol) of 2-bromochlorobenzene in 75 ml of dry tetrahydrofuran was chilled to -60° under N2 and stirred while 31 ml (0.05 mol) of 1.6 molar n-butyllithiumhexane solution was added at a rate that held the mixture below -55°. With continued cooling and stirring, 8.1 g (0.05 mol) of 4-bromochlorobenzene was added as a solid, followed by another 31 ml portion of the 1.6 molar n-butyllithium solution at a rate that held the mixture below -55° C. The resulting thin slurry was allowed to warm to room temperature, treated cautiously with 10 ml of ethyl acetate, and worked up as in Example 8 to give 15.0 g of a clear yellow oil. Distillation provided 5.9 g (37%) of the title compound: bp 150°-165° (0.7 mm); nD20 1.5916; ir (neat) 3060, 3020, 2960, 2920, 2870, 1580, 1560, 1490, 1420, 1380, 1255, 1125, 1115, 1085, 1035, 1015, 805, 750 cm-1 ; nmr (CDCl3) 0.8 (3H, s), 3.3 (2H, s), 7.2-7.7 (8H, m).

Workup

  1. additionwas added at a rate that
  2. customthe mixture below -55°
  3. temperatureWith continued cooling
  4. customthe mixture below -55° C

Sources & evidence

ORD record
ord-0c7ade39782f4c489410a7f9b31f2606
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

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