Carbon Dioxide → 3,6-Difluoro-2-methoxybenzoic acid

HRID 508189Notes

Reaction equation

HRID 508189 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH3:10].[Li+].CC([N-]C(C)C)C.[Li]CCCC.C(NC(C)C)(C)C.[C:31](=[O:33])=[O:32].OS(O)(=O)=O>C1COCC1.C(OCC)C>[F:1][C:2]1[C:3]([O:9][CH3:10])=[C:4]([C:5]([F:8])=[CH:6][CH:7]=1)[C:31]([OH:33])=[O:32]

Participants

9

Reactant 6

HCID 280Carbon DioxideHCID 1118Sulfuric AcidHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 27249892,5-DifluoroanisoleHCID 178418339Butyllithium

Product 1

HCID 160942453,6-Difluoro-2-methoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,4-difluoro-2-methoxybenzene (i-6a) (2.88 g, 20 mmol) in THF (5 mL) was added to a solution of LDA freshly prepared from n-BuLi (10M solution in hexane, 2.2 mL, 22 mmol) and diisopropylamine (2.28 g, 22.8 mmol) in THF (20 mL) at −60° C. After 30 min, a freshly prepared solution of CO2 in diethyl ether (20 mL) was quickly added. Then aq. H2SO4 was added, and the resulting precipitate was collected and washed with H2O, and dried to give the title compound (i-6b) as white crystals. LCMS (ESI) calc'd for C8H6F2O3 [M+H]+: 189. found: 189.

Workup

  1. customthe resulting precipitate was collected
  2. washwashed with H2O
  3. customdried

Sources & evidence

ORD record
ord-5aafd660425941529d5bb7699d4bd151
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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