HCID 67042919, compound → HCID 67042563, compound

HRID 1429288Notes

Reaction equation

HRID 1429288 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([B:21]([OH:23])[OH:22])=[C:17]([F:24])[C:16]=2[F:25])=[CH:11][CH:10]=1)C1C=CC=CC=1>C1COCC1>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([B:21]([OH:23])[OH:22])=[C:17]([F:24])[C:16]=2[F:25])=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 67042919HCID 67042919, compound

Product 1

HCID 67042563HCID 67042563, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

27.0 g (79.4 mmol) of 4′-benzyloxy-2,3-difluorobiphenyl-4-boronic acid are hydrogenated to completion on palladium/active carbon catalyst in THF. The catalyst is filtered off, and the solvent is removed in vacuo. The crude product is heated to 80° C. with 110 ml of toluene/ethyl acetate (10:1) with stirring and filtered off with suction after cooling, giving 4′-hydroxy-2,3-difluorobiphenyl-4-boronic acid as a colourless solid, which is employed in the next step without further purification.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is removed in vacuo
  3. filtrationfiltered off with suction
  4. temperatureafter cooling

Sources & evidence

ORD record
ord-fbad10365eea4486bad1d7e5b6c10240
Source dataset
uspto-grants-2015_01
Patent number
US08940184B2

Reaction notes

Loading…