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Hydrochloric Acid → 2-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenylboronic acid

HRID 2218716
Notes
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Reaction equation

HRID 2218716 reaction equation
[Li]CCCC.Br[C:7]1[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=1[CH:9]=[C:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][CH2:13][C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]1=2.[B:29](OC(C)C)([O:34]C(C)C)[O:30]C(C)C.Cl>C1COCC1>[CH:21]1[C:12]2[CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:10](=[CH:9][C:8]3[CH:25]=[CH:26][CH:27]=[CH:28][C:7]=3[B:29]([OH:34])[OH:30])[C:11]=2[CH:24]=[CH:23][CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 597701175-(2-bromo-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneHCID 178418339Butyllithium

Product 1

HCID 597702652-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
-78 °C

Procedure

Add n-BuLi (1.6M in hexanes, 12.98 Ml, 20.76 mmol) portionwise (exothermic) to a solution of 5-(2-bromo-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (5.00 g, 13.84 mmol) in dry THF (50 Ml) at −78° C. under N2. Let stir at −78° C. for 30 min, then add triisopropyl borate (5.21 g, 27.68 mmol) and warm up to room temperature overnight. Add 50 Ml 1.00N HCl and stir for 15 min. Extract into ethyl acetate, dry (MgSO4) and concentrate organics to a brown foam. Recrystallize from boiling hexanes, then chromatograph on silica gel (40 g), eluting with 20% to 50% ethyl acetate/hexanes to afford the title compound as a white foam, mp 134.1° C. MS (ES) 325 (M−H); HPLC shows 82% purity.

Workup

  1. stirringstir for 15 min
  2. extractionExtract into ethyl acetate
  3. dry with materialdry (MgSO4)
  4. concentrationconcentrate organics to a brown foam
  5. customRecrystallize
  6. washchromatograph on silica gel (40 g), eluting with 20% to 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d113203c8ca34e238d0b0a89847b6841
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07411072B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes