Ethyl 6-bromo-1-benzothiophene-2-carboxylate → (6-Bromo-1-benzothiophen-2-yl)methanol

HRID 250265

Reaction equation

HRID 250265 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([Br:15])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Br:15][C:12]1[CH:13]=[CH:14][C:8]2[CH:7]=[C:6]([CH2:4][OH:3])[S:10][C:9]=2[CH:11]=1

Participants

4

Reactant 2

HCID 13567982Ethyl 6-bromo-1-benzothiophene-2-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 13567983(6-Bromo-1-benzothiophen-2-yl)methanolYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A −78° C. solution of 6-bromo-benzo[b]thiophene-2-carboxylic acid ethyl ester (5.75 g; 20.2 mmol) in THF (200 mL) is treated with diisobutylaluminum hydride (50.4 mL; 1.0 M) dropwise. The mixture is stirred at 0° C. for 10 minutes and quenched with HCl (1 M, 50 mL). The mixture is extracted with EtOAc (150 mL). The organic layer is dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified via flash chromatography eluting with 25% EtOAc/Hexanes. The appropriate fractions are combined and concentrated under reduced pressure to afford the title compound (2.92 g, 60%). 1H NMR (400 MHz, CDCl3): δ 7.95 (s, 1H), 7.68 (d, 1H), 7.42 (d, 1H), 7.18 (s, 1H), 4.90 (s, 2H).

Workup

  1. customquenched with HCl (1 M, 50 mL)
  2. extractionThe mixture is extracted with EtOAc (150 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified via flash chromatography
  7. washeluting with 25% EtOAc/Hexanes
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7762a1bfe42649fd88919eb498952b21
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Linked notes

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