Reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[C:17]([O-])(O)=O.[Na+]>CO.C1(C)C=CC=CC=1.O>[Br:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH3:17])=[O:11])=[CH:7][CH:8]=1Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of p-bromomethylphenylacetic acid (50.0 g, 218 mmol) in MeOH (125 g) and toluene (250 g), was added thionyl chloride (15.6 g) dropwise at 0° C. and stirred for 3 hr. Separately NaHCO3 (33 g, 393 mmol) was dissolved in water (540 g), mixed with toluene (200 g) and cooled to 0° C. The reaction solution described above was added dropwise to the mixture and stirred for 1 hr. The aqueous layer was removed and the organic layer washed with water. The solution was then concentrated under reduced pressure at a temperature below 40° C. to give the subtitle compound as a crude product (58.9 g) used directly in the following reaction. 1H NMR (DMSO-d6) δ 7.37 (d, 2H), 7.34 (d, 2H), 4.62 (s, 2H), 3.73 (s, 2H), 3.63 (s, 3H)
Workup
- additionabove was added dropwise to the mixture
- stirringstirred for 1 hr
- customThe aqueous layer was removed
- washthe organic layer washed with water
- concentrationThe solution was then concentrated under reduced pressure at a temperature below 40° C.
Sources & evidence
- ORD record
- ord-6c511b199ecd4ff0a0654ecc319f86ea
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895570B2
Linked notes
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