Hydrochloric Acid → HCID 68281404, compound

HRID 1425934Notes

Reaction equation

HRID 1425934 reaction equation
[CH3:1][C:2]1([CH3:23])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:18]=[C:17]([C:19](OC)=[O:20])[CH:16]=[CH:15][C:10]=2[C:11](OC)=[O:12])[O:3]1.[H-].C([Al+]CC(C)C)C(C)C.Cl>C(Cl)Cl>[CH3:7][C:6]1([CH3:8])[C:2]([CH3:1])([CH3:23])[O:3][B:4]([C:9]2[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[CH:15][C:10]=2[CH2:11][OH:12])[O:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 68648457HCID 68648457, compound

Product 1

HCID 68281404HCID 68281404, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

Dimethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)terephthalate (CVI) (2.60 g, 8.12 mmol) was dissolved in DCM (25 mL), flushed with argon and cooled to −10° C. A 1 M solution of diisobutylaluminum hydride in DCM (48.73 mL, 48.73 mmol) was then added dropwise and the reaction was stirred at 0° C. for 2 h. 1 N aqueous HCl (50 mL) was carefully added and stirred for 5 minutes. The reaction was extracted with DCM and the combined extracts were washed with brine, dried over anhydrous MgSO4 and concentrated to give (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-phenylene)dimethanol (CVII) (2.0 g, 7.57 mmol). The crude product was used without further purification for step 4.

Workup

  1. customflushed with argon
  2. stirringstirred for 5 minutes
  3. extractionThe reaction was extracted with DCM
  4. washthe combined extracts were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-284cb6e3e9cc48d89a3c75950c7e7dbc
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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