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Water → Benzo[c]phenanthren-5-ylboronic acid

HRID 1470907
Notes
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Reaction equation

HRID 1470907 reaction equation
Br[C:2]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[CH:6]=[CH:5][C:4]=2[CH:3]=1.[B:20](OC)([O:23]C)[O:21]C.O>CCCCCC.C1COCC1>[CH:19]1[C:14]2[C:13]3[C:12]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[CH:6]=[CH:5][C:4]=3[CH:3]=[C:2]([B:20]([OH:23])[OH:21])[C:15]=2[CH:16]=[CH:17][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 8470Trimethyl borateHCID 106624825-Bromobenzo[c]phenanthrene

Product 1

HCID 59622711Benzo[c]phenanthren-5-ylboronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

52 ml (130 mmol) of n-buthyllithium (2.5 M in n-hexane) are added dropwise to a suspension of 30.7 g (100 mmol) of 5-bromobenzo[c]phenanthrene in 1000 ml of THF at −78° C. with vigorous stirring, and the mixture is stirred for a further 2 h. 16.7 ml (150 mmol) of trimethyl borate are added to the red solution in one portion with vigorous stirring, the mixture is stirred at −78° C. for a further 30 min., then warmed to room temperature over the course of 3 h, 300 ml of water are added, and the mixture is stirred for 30 min. The organic phase is separated off and evaporated to dryness in vacuo. The solid is taken up in 100 ml of n-hexane, filtered off with suction, washed once with 100 ml of hexane and dried in vacuo. Yield: 24.8 g (91 mmol), 91%, purity about 90% (NMR) of boronic acid, with varying amounts of boronic anhydride and boronic acid. The boronic acid can be used in this form without further purification.

Workup

  1. stirringthe mixture is stirred at −78° C. for a further 30 min.
  2. additionare added
  3. stirringthe mixture is stirred for 30 min
  4. customThe organic phase is separated off
  5. customevaporated to dryness in vacuo
  6. filtrationfiltered off with suction
  7. washwashed once with 100 ml of hexane
  8. customdried in vacuo
  9. customThe boronic acid can be used in this form without further purification

Sources & evidence

ORD record
ord-237693dbcfab4ab296463d2378d4362c
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09006503B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes