Hydrochloric Acid → HCID 22065807, compound

HRID 1828619Notes

Reaction equation

HRID 1828619 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].Br[C:7]1[CH:12]=[CH:11][C:10]2C3C([C:19]4([CH:27]=[C:26]5[C:21]([CH:22]=[CH:23][CH:24]=[CH:25]5)=[CH:20]4)[C:9]=2[CH:8]=1)=CC=CC=3.[B:28]([O:37]C(C)C)([O:33]C(C)C)OC(C)C.Cl.[CH2:42]1COC[CH2:43]1>CCOCC.O>[CH:27]1[C:19]2([C:2]3[CH:43]=[C:42]([B:28]([OH:33])[OH:37])[CH:5]=[CH:4][C:3]=3[C:10]3[C:9]2=[CH:8][CH:7]=[CH:12][CH:11]=3)[CH:20]=[C:21]2[C:26]=1[CH:25]=[CH:24][CH:23]=[CH:22]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21531Triisopropyl borateHCID 22065788HCID 22065788, compoundHCID 178418339Butyllithium

Product 1

HCID 22065807HCID 22065807, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

n-BuLi (1.2 equiv) is added to a solution of 2-bromospiro(fluorene-9,2′-indene) (6a) in anhydrous THF at −78° C. After stirring the mixture for 1 h, triisopropyl borate (1.5 equiv) is added. The reaction mixture is allowed to warm to room temperature and then is stirred overnight. 2.0 N HCl (10 equiv) is added to quench the reaction. The reaction mixture is mixed with a large amount of water for extraction with ether. The organic extracts are washed with brine before drying over anhydrous MgSO4. After the solvent is evaporated, the crude product of (7a) is washed with hexane several times to yield a white powder (89%).

Workup

  1. stirringis stirred overnight
  2. customto quench
  3. customthe reaction
  4. washThe organic extracts are washed with brine
  5. dry with materialbefore drying over anhydrous MgSO4
  6. customAfter the solvent is evaporated
  7. washthe crude product of (7a) is washed with hexane several times

Sources & evidence

ORD record
ord-fcf4b4c024024c0b845bba658f44dc6c
Source dataset
uspto-grants-2006_06
Patent number
US07057009B2

Reaction notes

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