2-Methoxyethanol → 4-Bromo-1-fluoro-2-((2-methoxyethoxy)methyl)benzene

In a 10 ml flask, under a nitrogen atmosphere, 2-methoxyethanol (0.125 ml, 1.60 mmol) was dissolved in N,N-dimethylformamide (2 ml). Sodium hydride (60%, 72 mg, 1.81 mmol) was added and the mixture was stirred at ambient temperature for about thirty minutes. To this reaction mixture was added 2-fluoro-5-bromobenzyl bromide (285 mg, 1.06 mmol) as a solution in N,N-dimethylformamide (2 ml). The resulting mixture was stirred at ambient temperature for two hours. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was partitioned between 1 M potassium carbonate and diethyl ether. The aqueous fraction was back extracted with diethyl ether. The organic fractions were combined, washed with brine (7×) and dried over sodium sulfate. The solvents were removed in vacuo. The title intermediate was used without further purification.

1. stirringThe resulting mixture was stirred at ambient temperature for two hours
2. customThe reaction mixture was partitioned between 1 M potassium carbonate and diethyl ether
3. extractionThe aqueous fraction was back extracted with diethyl ether
4. washwashed with brine (7×)
5. dry with materialdried over sodium sulfate
6. customThe solvents were removed in vacuo
7. customThe title intermediate was used without further purification

ORD record

ord-8d4aedb595f646e3995a07210fd6b336

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245761B1