3-Bromoaniline → 1-(3-Bromophenyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane

HRID 1975512Notes

Reaction equation

HRID 1975512 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH3:9][Si:10]([CH3:26])(N(CC)CC)[CH2:11][CH2:12][Si:13]([CH3:20])([CH3:19])N(CC)CC>>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[Si:13]([CH3:20])([CH3:19])[CH2:12][CH2:11][Si:10]2([CH3:26])[CH3:9])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 115623-BromoanilineHCID 12655956HCID 12655956, compound

Product 1

HCID 132686651-(3-Bromophenyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane

Procedure

The alpha,omega-aniline terminated dimethyl siloxanes are prepared, starting with 3-bromoaniline, in which the amine functionality is protected, such as by reaction with 1,1,4,4-tetramethyl-1,4-bis(N,N-diethylamino)-1,4-disilabutane, to form 1-(3-bromophenyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane. The protected bromoaniline is then reacted with an alkyllithium or with magnesium to form the corresponding lithio or Grignard compound, respectively, which is then reacted with chlorodialkylsilane to form 1-(3-(dialkylsilyl)phenyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane. This reaction places the silane functionality in the meta position. Next, the protected dimethylsilane aniline is subjected to deprotection to form 3-aminophenyldialkyl silane, which is considered to be novel. This silane is then hydrolyzed to form the corresponding silanol, also considered to be novel. The silanol is then condensed to form bis(3-aminophenyl)-1,1,3,3-tetraalkyldisiloxane.

Workup

  1. customThe alpha,omega-aniline terminated dimethyl siloxanes
  2. customare prepared

Sources & evidence

ORD record
ord-8c8efa0f3da64925adf618be14b3b859
Source dataset
uspto-grants-1994_02
Patent number
US05286890

Reaction notes

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