Sodium Hydroxide → HCID 67003504, compound

HRID 2199698Notes

Reaction equation

HRID 2199698 reaction equation
[OH-].[Na+].[Br:3][C:4]1[C:12]2[S:11][C:10]([C:13]([O:15]C)=[O:14])=[CH:9][C:8]=2[CH:7]=[C:6]([C:17]([F:20])([F:19])[F:18])[CH:5]=1>O1CCOCC1>[Br:3][C:4]1[C:12]2[S:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][C:8]=2[CH:7]=[C:6]([C:17]([F:20])([F:18])[F:19])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67003514HCID 67003514, compound

Product 1

HCID 67003504HCID 67003504, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of NaOH (4.0 M in water, 5.0 mL, 20 mmol) was added to a solution of methyl 7-bromo-5-(trifluoromethyl)-1-benzothiophene-2-carboxylate (1.00 g, 2.95 mmol) in dioxane (11 mL). The mixture was heated at 70° C. overnight, allowed to cool to room temperature, then concentrated. The resulting light beige solid was partitioned between water (25 mL) and 1:1 hexanes:ethyl acetate (15 mL). The resulting layers were separated. The aqueous layer was adjusted to pH 2 with 2.0 M HCl (aq) then extracted four times with CH2Cl2. The combined CH2Cl2 layers were dried over Na2SO4, filtered, then concentrated. The resulting acid, a light yellow solid, was used directly for the following step. LC1: 3.58 min. Compound does not ionize.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated
  3. customThe resulting light beige solid was partitioned between water (25 mL) and 1:1 hexanes
  4. customThe resulting layers were separated
  5. extractionthen extracted four times with CH2Cl2
  6. dry with materialThe combined CH2Cl2 layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custom3.58 min

Sources & evidence

ORD record
ord-546bdd7f562f49afb31e9b545c45d624
Source dataset
uspto-grants-2016_06
Patent number
US09359339B2

Reaction notes

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