Sulfuric Acid → HCID 16094239, compound

HRID 508190Notes

Reaction equation

HRID 508190 reaction equation
[F:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([C:8]([F:11])=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Li+].CC([N-]C(C)C)C.C(NC(C)C)(C)C.[Li]CCCC.[B:34](OCC)([O:38]CC)[O:35]CC.OS(O)(=O)=O>C1COCC1>[B:34]([C:10]1[CH:9]=[C:8]([F:11])[C:4]([C:5]([OH:7])=[O:6])=[C:3]([O:12][CH3:13])[C:2]=1[F:1])([OH:38])[OH:35]

Participants

8

Reactant 6

HCID 1118Sulfuric AcidHCID 7912DiisopropylamineHCID 9009Triethyl borateHCID 2724682Lithium diisopropylamideHCID 160942453,6-Difluoro-2-methoxybenzoic acidHCID 178418339Butyllithium

Product 1

HCID 16094239HCID 16094239, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3,6-difluoro-2-methoxybenzoic acid (i-6b) (0.94 g, 5 mmol) in THF (5 mL) at −70° C. was added a solution of LDA [freshly prepared from diisopropylamine (1.51 g, 15 mmol) and n-BuLi (10M solution in hexane, 1.5 mL, 15 mol) in THF (15 mL). The resultant solution was stirred for 15 mins, followed by the addition of B(OEt)3 (1.46 g, 10 mmol). The mixture was stirred for 15 mins and then hydrolyzed with dilute aq. H2SO4. The organic phase was separated and the aqueous layer was extracted with Et2O. The combined organics were concentrated and the residue solid was washed with H2O and hexane, dried to give the title compound as white crystals. LCMS (ESI) calc'd for C8H7BF2O5 [M+H]+: 233. found: 233.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted with Et2O
  3. concentrationThe combined organics were concentrated
  4. washthe residue solid was washed with H2O and hexane
  5. customdried

Sources & evidence

ORD record
ord-b6f5f043948143d59c16cb465ffc0948
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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