Tavaborole → 6-Fluorobenzo[c][1,2]oxaborol-1(3H)-ol

HRID 424376Notes

Reaction equation

HRID 424376 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][O:10]COC.FC1C=CC2[B:22](O)[O:21]CC=2C=1>>[F:8][C:6]1[CH:5]=[CH:4][C:3]2[CH2:9][O:10][B:22]([OH:21])[C:2]=2[CH:7]=1

Participants

3

Reactant 2

HCID 11499245TavaboroleHCID 667046952-Bromo-4-fluoro-1-(methoxymethoxymethyl)benzene

Product 1

HCID 118461196-Fluorobenzo[c][1,2]oxaborol-1(3H)-ol

Procedure

This compound was made from 18m in the same manner as compound 19b: 1H NMR (300 MHz, DMSO-d6) δ (ppm) 4.95 (s, 2H), 7.29 (td, J=9.0, 2.7 Hz, 1H), 7.41-7.46 (m, 2H), 9.29 (s, 1H); ESI-MS m/z 151 (M−H)−; HPLC purity 100%; Anal (C7H6BFO2) C, H.

Sources & evidence

ORD record
ord-5493b7950b6546aaa9ad4e19d8e78bea
Source dataset
uspto-grants-2012_01
Patent number
US08106031B2

Reaction notes

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