Sodium Hydroxide → HCID 57936575, compound

HRID 1434876Notes

Reaction equation

HRID 1434876 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]([CH2:13][S:14][CH3:15])[CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]([CH2:13][S:14][CH3:15])[CH:10]=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 57936639HCID 57936639, compound

Product 1

HCID 57936575HCID 57936575, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a −78° C. mixture of methyl 2-methoxy-4-(methylthio-methyl)benzoate (5.29 (g, 23.36 mmol) and CH2Cl2 (80 mL) was added BBr3 (2.4 mL, 24.52 mmol) dropwise. The reaction was stirred for 15 min, warmed to room temperature and stirred for 6 h. The reaction mixture was added to ice/water (100 mL). The suspension was added 2 M NaOH to dissolve the precipitate. After partitioning, the organic layer was extracted with 2 M NaOH. The combined aqueous layer was washed with EtOAc, acidified with 12 N HCl and cooled to room temperature. The solid was filtered with water wash and vacuum dried to give the title compound as a light yellow solid (2.96 g, 64%).

Workup

  1. stirringstirred for 6 h
  2. dissolutionto dissolve the precipitate
  3. customAfter partitioning
  4. extractionthe organic layer was extracted with 2 M NaOH
  5. washThe combined aqueous layer was washed with EtOAc
  6. temperaturecooled to room temperature
  7. filtrationThe solid was filtered with water
  8. washwash
  9. customvacuum dried

Sources & evidence

ORD record
ord-25569d43b59849538df0cd86b5a48cda
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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