Boron tribromide → 6-Hydroxy-n,2-dimethyl-1-benzothiophene-3-carboxamide

HRID 985188Notes

Reaction equation

HRID 985188 reaction equation
B(Br)(Br)Br.[CH3:5][NH:6][C:7]([C:9]1[C:10]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][C:11]=2[S:12][C:13]=1[CH3:14])=[O:8]>C(Cl)Cl>[CH3:5][NH:6][C:7]([C:9]1[C:10]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:11]=2[S:12][C:13]=1[CH3:14])=[O:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 207678726-Methoxy-N,2-dimethyl-1-benzothiophene-3-carboxamide

Product 1

HCID 207678636-Hydroxy-n,2-dimethyl-1-benzothiophene-3-carboxamideYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1.0 M solution of BBr3 in CH2Cl2 (6 ml, 6 mmole) was added to a solution of 6-methoxy-2-methylbenzo[b]thiophene-3-carboxylic acid methylamide 1c (683 mg, 2.9 mmole) in CH2Cl2 (60 ml) at 0°. The reaction was left stirring for 14 hours, gradually warming to ambient temperature, then poured onto crushed ice (˜70 g). The layers were separated and the aqueous phase was extracted with EtOAc (2×50 ml). The combined organic extracts were dried over Na2SO4 and concentrated, in vacuo, to give 623 mg (97%) of a beige solid which was employed without further purification. 1H NMR (DMSO-d6) δ9.56 (1H, s), 8.11 (1H, q, J=4.4 Hz), 7.53 (1H, d, J=8.7 Hz), 7.18 (1H, d, J=2.3 Hz), 6.83 (1H, dd, J=2.3, 8.7 Hz), 2.79 (3H, d, J=4.4 Hz), 2.50 (3H, s).

Workup

  1. waitThe reaction was left
  2. additionpoured
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc (2×50 ml)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated, in vacuo

Sources & evidence

ORD record
ord-c1d5b50726884bc1abbcc28cea4e4d08
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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