Ethanol → HCID 18315947, compound

HRID 275770Notes

Reaction equation

HRID 275770 reaction equation
[Cl:1][C:2]1[C:3]2[CH:15]=[C:14]([O:16]C)[CH:13]=[CH:12][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].B(Br)(Br)Br.C(O)C>ClCCl>[Cl:1][C:2]1[C:3]2[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 25134Boron tribromideHCID 2801563HCID 2801563, compound

Product 1

HCID 18315947HCID 18315947, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of ethyl 3-chloro-5-methoxybenzo[b]thiophene-2-carboxylate (20.0 g) in dichloromethane (80 ml) at −20° C. under an atmosphere of nitrogen was treated with boron tribromide (1 M solution in dichloromethane; 90 ml) and the solution allowed to warm up to room temperature slowly. After 2 hours the mixture was carefully poured into ethanol (400 ml) and left to stand for 10 minutes. The solvent was evaporated under reduced pressure and the residue dissolved in ethyl acetate (500 ml). The resulting solution was washed with water (300 ml), dried over sodium sulphate and the solvent evaporated under reduced pressure to give ethyl 3-chloro-5-hydroxybenzo[b]thiophene-2-carboxylate (18.68 g) as an off-white solid; m.p. 160-161° C.

Workup

  1. waitleft
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue dissolved in ethyl acetate (500 ml)
  4. washThe resulting solution was washed with water (300 ml)
  5. dry with materialdried over sodium sulphate
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-efad9c1306f443d19d4428a124a946cc
Source dataset
uspto-grants-2002_03
Patent number
US06353002B2

Reaction notes

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