Benzoyl chloride, 3-bromo- → tert-Butyl 3-bromobenzoate

In an oven dried, 1-L, 3-necked round bottom flask equipped with an addition funnel, a glass stopper, a magnetic stirbar, and a reflux condenser connected to a nitrogen inlet, potassium t-butoxide (23.6 g, 209.6 mmol) was combined with toluene (150 mL). A solution of 3-bromobenzoyl chloride (40 g, 182.3 mmol) in toluene (100 mL) was added dropwise to the potassium t-butoxide and the mixture was stirred for 16 h at room temperature. The viscous mixture was transferred to a 1-L separatory funnel, and the reaction flask was rinsed with toluene (50 mL) and added to the separatory funnel. The toluene mixture was extracted with water (200 mL), a potassium carbonate solution (10%, 250 mL), and again with water (3×200 mL). The toluene layer was dried over magnesium sulfate and filtered, and the toluene was removed in vacuo to yield the product as a yellow oil (45.1 g, 96%). HPLC: >99% pure.

1. customIn an oven dried
2. custom1-L, 3-necked round bottom flask equipped with an addition funnel
3. customa glass stopper, a magnetic stirbar, and a reflux condenser connected to a nitrogen inlet
4. customThe viscous mixture was transferred to a 1-L separatory funnel
5. washthe reaction flask was rinsed with toluene (50 mL)
6. additionadded to the separatory funnel
7. extractionThe toluene mixture was extracted with water (200 mL)
8. dry with materialThe toluene layer was dried over magnesium sulfate
9. filtrationfiltered
10. customthe toluene was removed in vacuo

ORD record

ord-5439fc6cd5624f2db39f2670c580347a

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399504B2