Sciencemadness Discussion Board

Bromoacetyl Bromide

liftedresearch - 19-11-2015 at 19:45

Hello all,

I have been looking everywhere for the synthesis of Bromoacetyl Bromide(CAS No. 598-21-0) without the use of Red Phosphorous. I have found the synthesis of using RP, but I dont have any RP. So if any of you wonderful ladys/gentlemen know of one it would be much obliged.

(P.S. Feel free to move this thread if I have posted it in the wrong area)

karlosĀ³ - 19-11-2015 at 22:15

You could use PBr3 or PBr5 if you can buy this.

gdflp - 20-11-2015 at 07:15

OrgSyn has a preparation of bromoacetic acid from acetic acid. From there, you could try sulfur monobromide to brominate the acid to the acid bromide.

byko3y - 20-11-2015 at 13:37

What's your starting coupound(s)? Thionyl bromide, anhydride+HBr, oxalyl bromide can be used to convert bromoacetic acid to bromoacetyl bromide.

AvBaeyer - 20-11-2015 at 19:21

If you can use bromoacetyl CHLORIDE, you can make acid chlorides from triphenylphosphine and trichloroisocyanuric acid (TCCA). You would still need to get your hands on bromoacetic acid. The reference is shown below.

SYNTHETIC COMMUNICATIONS, 29(8), 1415-1419 (1999)

Using the Appel reaction which is triphenylphosphine and carbon tetrahalide will give the acid chloride (CCl4) or acid bromide (CBr4). A leading reference is

JACS 88, 3440 (1966)

AvB