Bromotrimethylsilane → (4-Hydroxyphenyl)phosphonic acid

HRID 889679노트

반응식

HRID 889679 반응식
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]

참가 물질

4

반응물 2

HCID 76113BromotrimethylsilaneHCID 2773718p-Diethoxyphosphorylphenol

생성물 1

HCID 214694(4-Hydroxyphenyl)phosphonic acid

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9f214753304a471ca01b2193366016ac
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252954B2

반응 노트

불러오는 중…