Hydrochloric Acid → HCID 66571441, compound

HRID 924670Notes

Reaction equation

HRID 924670 reaction equation
C([Mg]Cl)(C)C.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[C:9](I)[CH:8]=1.C[O:18][B:19](OC)[O:20]C.Cl>C1COCC1>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[C:9]([B:19]([OH:20])[OH:18])[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 68402691HCID 68402691, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 66571441HCID 66571441, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

i-Propylmagnesium chloride (2 M in THF, 3.34 mL, 6.7 mmol) was added drop wise to a solution of 4-chloro-2-iodo-1-(propan-2-yl)benzene (1.7 g, 6.7 mmol) in dry THF (15 mL) at −30° C. and the reaction mixture was stirred at the same temperature for 30 min, under argon. After this time, trimethylborate (1.35 mL, 12.1 mmol) was added drop wise and the reaction mixture was stirred at the same temperature for 1.5 h. HCl (1 M, 6 mL) was added and the reaction mixture extracted with EtOAc (3×20 mL). The combined organic layers were dried over sodium sulfate and, after removal of the solvent, a solid was obtained, which was triturated with hexane to obtain the title compound as a white solid (1.05 g, 87%).

Workup

  1. stirringthe reaction mixture was stirred at the same temperature for 1.5 h
  2. extractionthe reaction mixture extracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customafter removal of the solvent
  5. customa solid was obtained
  6. customwhich was triturated with hexane

Sources & evidence

ORD record
ord-d2e41411e42d474298eb60eaced23ca7
Source dataset
uspto-grants-2016_03
Patent number
US09283224B2

Reaction notes

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