Triisopropyl borate → 2,3-Difluoro-4-octoxybiphenyl-4'-yl-boronic acid

HRID 343255Notes

Reaction equation

HRID 343255 reaction equation
FC1C(F)=C(OCCCCCCCC)C=CC=1[B:18]([OH:20])[OH:19].Br[C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[C:30]([F:43])[C:29]=2[F:44])=[CH:24][CH:23]=1.C([Li])CCC.C(OB(OC(C)C)OC(C)C)(C)C>>[F:44][C:29]1[C:30]([F:43])=[C:31]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:32]=[CH:33][C:28]=1[C:25]1[CH:26]=[CH:27][C:22]([B:18]([OH:20])[OH:19])=[CH:23][CH:24]=1

Participants

5

Reactant 4

HCID 21531Triisopropyl borateHCID 10620805HCID 10620805, compoundHCID 10850744(2,3-Difluoro-4-(octyloxy)phenyl)boronic acidHCID 178418339Butyllithium

Product 1

HCID 106899942,3-Difluoro-4-octoxybiphenyl-4'-yl-boronic acid

Procedure

This was prepared using a similar method to that described for compound 5. Quantities: 4'-bromo-2,3-difluoro-4-octoxybiphenyl (8) (3.18g, 8.0 mmol), n-butyllithium (3.2 ml, 2.5M/hexane, 8.0 mmol), tri-isopropylborate (3.01 g, 16.0 mmol).

Workup

  1. customThis was prepared

Sources & evidence

ORD record
ord-164c150a563b4855bd8fcb4436655ab9
Source dataset
uspto-grants-1999_01
Patent number
US05861109

Reaction notes

Loading…