Bromotrimethylsilane → Phosphonic acid, (p-hydroxyphenyl)-

HRID 889679ノート

反応式

HRID 889679 の反応式
Br[Si](C)(C)C.C([O:8][P:9]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([O:11]CC)=[O:10])C>C(#N)C>[OH:10][P:9]([C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)([OH:11])=[O:8]

参加物

4

反応物 2

HCID 76113BromotrimethylsilaneHCID 2773718p-Diethoxyphosphorylphenol

生成物 1

HCID 214694Phosphonic acid, (p-hydroxyphenyl)-

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Bromotrimethylsilane (1 ml) was added to 24 (0.5 g) in dry acetonitrile (10 ml) and the solution was refluxed for 24 h. The volatiles were removed under reduced pressure and acetonitrile (20 ml) was added to the residue and the solution stirred for 1 hour. The volatiles were removed under reduced pressure to yield 25 in quantitative yield, which was used without further purification in the next step. 1H NMR (DMSO-d6, 25° C., 500 MHz) δ 8.6 (br s, 3H, COH/POH), 7.49 (dd, 2H, ArH, J=12.5/8.5 Hz), 6.81 (dd, 2H, ArH, J=8.5/3.0 Hz); 13C NMR (DMSO-d6, 25° C., 126 MHz) δ 159.82 (d, 4JP-C=3.3 Hz), 132.52 (d, 2JP-C=11.3 Hz), 123.47 (d, 1JP-C=189.4 Hz), 114.92 (d, 3JP-C=15.3 Hz); 31P NMR (DMSO-d6, 25° C., 243 MHz) δ 14.69. Crystal/refinement details for 25a: C10H15O4P, M=230.19, F (000)=488 e, monoclinic, P21/n (No. 14), Z=4, T=100(2) K, a=8.5520(3), b=15.5263(4), c=8.6384(2) Å, β=92.433(2)°, V=1145.98(6) Å3, Dc=1.334 gcm−3, μMo=0.232 mm−1, sin θ/λmax=0.7035, N (unique)=3340 (merged from 13120, Rint=0.0303, Rsig=0.0306), No (I>2σ(I))=2694, R=0.0350, wR2=0.0948 (A, B=0.06, 0.1), GOF=1.003, |Δρmax|=0.41(6) e Å−3.

後処理

  1. temperaturethe solution was refluxed for 24 h
  2. customThe volatiles were removed under reduced pressure and acetonitrile (20 ml)
  3. additionwas added to the residue
  4. customThe volatiles were removed under reduced pressure

出典と根拠

ORDレコード
ord-9f214753304a471ca01b2193366016ac
出典データセット
uspto-grants-2012_08
特許番号
US08252954B2

反応ノート

読み込み中…