Isopropanol → 1-Bromo-4-((propan-2-yloxy)methyl)benzene

60% Sodium hydride in mineral oil (0.96 g, 24 mmol) was added to a solution of isopropanol (7.59 mL, 36 mmol) in dry N,N-dimethylformamide (30 mL) at 0° to 5° C. under argon atmosphere. After the mixture was stirred for about 25 minutes, 4-bromo-benzyl bromide was added and the mixture stirred at 20° C. for an additional 1 hour. The solution was partitioned between saturated ammonium chloride (50 mL) and diethyl ether (50 mL). The aqueous phase was extracted with diethyl ether (3×20 mL), and the combined organic layers were washed with water, dried (Na2SO4), and evaporated in vacuo. The crude product was filtered over silica gel to give pure 1-bromo-4-isopropoxymethylbenzene (2.33 g, 85%) as clear oil.

1. stirringthe mixture stirred at 20° C. for an additional 1 hour
2. customThe solution was partitioned between saturated ammonium chloride (50 mL) and diethyl ether (50 mL)
3. extractionThe aqueous phase was extracted with diethyl ether (3×20 mL)
4. washthe combined organic layers were washed with water
5. dry with materialdried (Na2SO4)
6. customevaporated in vacuo
7. filtrationThe crude product was filtered over silica gel

ORD record

ord-a2428da032af4e9386b75ecbe2fa497d

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06693200B2