Dimethylformamide → HCID 90418305, compound

HRID 2177337Notes

Reaction equation

HRID 2177337 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[CH2:13][OH:14])=[CH:4][CH:3]=1.CN(C)C=O.C1C(=O)N([Br:27])C(=O)C1>CC(=O)OCC>[Br:27][C:11]1[S:10][C:9]([CH2:13][OH:14])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 90418164HCID 90418164, compound

Product 1

HCID 90418305HCID 90418305, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Into a 100-mL round-bottom flask, was placed [3-(4-chlorophenyl)thiophen-2-yl]methanol (3.6 g, 16.02 mmol, 1.00 equiv), N,N-dimethylformamide (20 mL). This was followed by the addition of NBS (2.85 g, 16.01 mmol, 1.00 equiv) portions at −5° C. The resulting solution was stirred for 2 h at room temperature (20 degree C.). The resulting solution was diluted with 100 mL of EA. The resulting mixture was washed with 3×30 mL of brine. The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). This resulted in 4.8 g (99%) of [5-bromo-3-(4-chlorophenyl)thiophen-2-yl]methanol as a yellow solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. washThe resulting mixture was washed with 3×30 mL of brine
  3. dry with materialThe mixture was dried over anhydrous sodium sulfate
  4. filtrationThe solids were filtered out
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThis resulted in 4.8 g (99%) of [5-bromo-3-(4-chlorophenyl)thiophen-2-yl]methanol as a yellow solid

Sources & evidence

ORD record
ord-e2f7d49e35ce40fdba0e0778d6a333d1
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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