Tavaborole → 5-(Hydroxymethyl)benzo[c][1,2]oxaborol-1(3h)-ol

HRID 424375Notes

Reaction equation

HRID 424375 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9]COC)=[CH:4][C:3]=1[CH2:13][O:14]COC.FC1C=CC2[B:26](O)[O:25]CC=2C=1>>[OH:25][B:26]1[C:2]2[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=2[CH2:13][O:14]1

Participants

3

Reactant 2

HCID 11499245TavaboroleHCID 667047472-Bromo-1,5-bis(methoxymethoxymethyl)benzene

Product 1

HCID 118457515-(Hydroxymethyl)benzo[c][1,2]oxaborol-1(3h)-ol

Procedure

This compound was made from 18h in the same manner as compound 19b: mp 124-128° C.; 1H NMR (300 MHz, DMSO-d6) δ (ppm) 4.53 (d, 2H), 4.94 (s, 2H), 5.24 (t, 1H), 7.26 (d, 1H), 7.33 (s, 1H), 7.64 (d, 1H), 9.08 (s, 1H); ESI-MS m/z 163 (M−H)−; HPLC purity 100%.

Sources & evidence

ORD record
ord-e402c0c8508f4d01ab14c0db418536e4
Source dataset
uspto-grants-2012_01
Patent number
US08106031B2

Reaction notes

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