Ammonium → (5-Bromo-1-benzofuran-2-yl)methanol

HRID 1171212Notes

Reaction equation

HRID 1171212 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].C([O:13][C:14]([C:16]1[O:17][C:18]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][C:19]=2[CH:20]=1)=O)C.[NH4+]>O1CCCC1>[Br:25][C:22]1[CH:23]=[CH:24][C:18]2[O:17][C:16]([CH2:14][OH:13])=[CH:20][C:19]=2[CH:21]=1

Participants

6

Reactant 4

HCID 223AmmoniumHCID 735184Ethyl (5-bromobenzofuran)-2-carboxylateHCID 6451240Aluminum(III) Chloride2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 2795537(5-Bromo-1-benzofuran-2-yl)methanolYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a tetrahydrofuran (20 mL) solution of lithium aluminum hydride (706 mg, 18.6 mmol) was added aluminum chloride (2.98 g, 22.3 mmol), which was stirred until the aluminum chloride dissolved in tetrahydrofuran. Then, to the reaction mixture was added 5-bromo-benzofuran-2-carboxylic acid ethyl ester (1.00 g, 3.72 mmol) described in Production Example 56-1-1 at 0° C. followed by stirring at 0° C. for 20 minutes. To the reaction solution was added aqueous ammonium followed by filtering through Celite. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (780 mg, 92%) as a white solid.

Workup

  1. customdescribed in Production Example 56-1-1 at 0° C.
  2. filtrationby filtering through Celite
  3. concentrationThe filtrate was concentrated under a reduced pressure
  4. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-595ada0553774968b33caed3e83ca3cc
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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