Toluene → 1-(2-Bromoethyl)-4-chlorobenzene

A 500 ml. 3 neck round bottomed flask under nitrogen was charged 15.65 g. of 4-chlorophenethanol (1.0 eq., 0.10 moles) in 60 ml. toluene. To the reaction was added dropwise 41.6 g of thionyl bromide (2.0 eq., 0.20 moles) in 15 ml. of toluene maintaining the temp. below 25 C. Finally, 8.7 g. pyridine (1.1 eq., 0.11 moles) in 20 ml. toluene was added dropwise again keeping the temperature below 30° C. with an external ice bath. The reaction was monitored by GLC and after 1 hr. an additional 14.0 g of thionyl bromide (0.67 eq. 0.067 moles) was added followed three hours later by 9.7 gms. (1.1 eq., 0.11 moles). Subsequently 4.3 g. of pyridine was added (0.55 eq., 0.055 moles) after which GLC indicated all the alcohol was consumed. The reaction was quenched by the addition of 300 ml of water while cooling with an ice bath after which 400 ml. of ether was added. The ether was washed water three times with 250 ml.), dried over MgSO4 and concentrated to give 14.4 g of product as an oil (65.2% yield).

1. addition3 neck round bottomed flask under nitrogen was charged 15.65 g
2. customthe temperature below 30° C.
3. waitfollowed three hours later by 9.7 gms
4. customwas consumed
5. customThe reaction was quenched by the addition of 300 ml of water
6. temperaturewhile cooling with an ice bath after which 400 ml
7. additionof ether was added
8. washThe ether was washed water three times with 250 ml
9. dry with material), dried over MgSO4
10. concentrationconcentrated

ORD record

ord-37ea8b1c80c34dddbf3731b7e1c707e9

Source dataset

uspto-grants-1995_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05397793