4-Bromothiophene-2-carbaldehyde → HCID 57908828, compound

HRID 1259438Notes

Reaction equation

HRID 1259438 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[S:5][CH:6]=1.[Li+].C[Si]([N-:14][Si](C)(C)C)(C)C.[CH2:19]([Mg]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]([NH2:14])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 877924-Bromothiophene-2-carbaldehydeHCID 2733832Lithium HexamethyldisilazideHCID 178418336HCID 178418336, compound

Product 1

HCID 57908828HCID 57908828, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 4-bromothiophene-2-carboxaldehyde (10.1 g, 52.8 mmol) in anhydrous THF (150 mL) at 0° C. under N2 was added dropwise 1.0 M LiHMDS (58 mL) in THF. After 30 min, a solution of 2.0 M benzylmagnesium chloride (27 mL) in THF was added dropwise. The resulting mixture was stirred at rt for 50 min. The reaction mixture was quenched with sat. NH4Cl and most of the THF was evaporated. The residue was diluted with ethyl acetate (150 mL), washed with water and brine, and dried over MgSO4. Purification by flash chromatography gave 1A as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ: 1.5 (s, broad, 2H), 2.8 (m, 1H), 3.08 (m, 1H), 4.4 (m, 1H), 6.8 (s, 1H), 7.1-7.3 (m, 6H).

Workup

  1. customThe reaction mixture was quenched with sat. NH4Cl and most of the THF
  2. customwas evaporated
  3. additionThe residue was diluted with ethyl acetate (150 mL)
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-89636ba864194f2b8dfc32becbcf86a3
Source dataset
uspto-grants-2013_06
Patent number
US08466295B2

Reaction notes

Loading…