Bromotrimethylsilane → Phosphonic acid, (p-hydroxyphenyl)-

Participants

Reaction Steps

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.

Provenance & Evidence