Water → HCID 66611909, compound

HRID 2204683Notes

Reaction equation

HRID 2204683 reaction equation
[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:12])[CH:3]=1.S(Cl)(Cl)=O.[CH2:17](Cl)Cl.O>CO>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([OH:12])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 66611693HCID 66611693, compound

Product 1

HCID 66611909HCID 66611909, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-bromo-2-hydroxy-5-methylbenzoic acid (may be prepared as described in Description 13; 1.47 g, 6.36 mmol) in methanol (15 ml) was added thionyl chloride (0.93 ml, 12.72 mmol). The reaction was heated at 50° C. for 72 hours, then DCM (20 ml) and water (10 ml) were added. The organic layer was separated and washed with saturated NaHCO3 solution (10 ml), dried (MgSO4) and the solvent removed in vacuo to yield the title compound as a white solid. 1.2 g.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated NaHCO3 solution (10 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ea67bd62216a4a71bcbc0c1275de9c6a
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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