Hydrochloric Acid → (5,6-difluoro-2,2-dimethyl-3H-benzofuran-7-yl)methanol

HRID 1909587Notes

Reaction equation

HRID 1909587 reaction equation
[F:1][C:2]1[C:3]([F:16])=[C:4]([C:13](O)=[O:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1.Cl.[OH-].[Na+]>>[F:1][C:2]1[C:3]([F:16])=[C:4]([CH2:13][OH:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[CH:12]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 585663065,6-difluoro-2,2-dimethyl-3H-benzofuran-7-carboxylic acid

Product 1

HCID 58566591(5,6-difluoro-2,2-dimethyl-3H-benzofuran-7-yl)methanolYield 57%

Procedure

To 5,6-difluoro-2,2-dimethyl-3H-benzofuran-7-carboxylic acid (735) (0.75 g, 3.29 mmol) was added 1.0 M of borane tetrahydrofuran complex solution (12 mL), and the mixture was stirred at room temperature overnight. The reaction was cooled to 0° C., acidified with 5 N HCl to pH 1, and then neutralized to pH 8 with 5 N NaOH. The mixture was extracted with EtOAc (80 mL×3) and the combined organic phase was washed with water (50 mL), dried over anhydrous sodium sulfate, and the solvent removed in vacuo. The product was purified by prep HPLC to yield (5,6-difluoro-2,2-dimethyl-3H-benzofuran-7-yl)methanol (736) (0.4 g, 57%). 1H NMR (400 MHz, DMSO-d6) δ 7.18 (t, J=9.0 Hz, 1H), 4.38 (s, 2H), 2.97 (s, 2H), 1.40 (s, 6H).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. extractionThe mixture was extracted with EtOAc (80 mL×3)
  3. washthe combined organic phase was washed with water (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent removed in vacuo
  6. customThe product was purified by prep HPLC

Sources & evidence

ORD record
ord-80bf698a965c410fa05df1ff50f7cdee
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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