Butyl bromide → HCID 131722455, compound
Reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5]O)[CH2:3][OH:4].[CH2:8](Br)[CH2:9][CH2:10][CH3:11].O=S(Cl)[Cl:15]>>[CH2:8]([O:4][CH2:3][C:2]([CH2:5][Cl:15])([CH3:7])[CH3:1])[CH2:9][CH2:10][CH3:11]Participants
Procedure
The alkylation of 2,2-dimethyl-1,3-propanediol with n-butyl bromide carried out essentially as in Example 8 gave the crude mono-alkylated product, which was treated with SOCl2 to give C4H9—O—CH2C(CH3)2CH2Cl, b. 80-90° C./20-30 torr. This compound was then fluorinated as in Example 1 to give C4F9—O—CF2C(CF3)2CF2Cl. 20.0 g of the latter chloride was mixed with 5.3 g water-wet Raney Ni and 50 mL of NH3-saturated methanol. The mixture was left shaking on a Parr hydrogenation apparatus for 3 days at about 25° C., with most of the 21 kPa (3 psig) hydrogen pressure drop occurring in the first day. The product was recovered by filtration and quenched in water, yielding 7.9 g with some mechanical loss. 19F-nmr confirmed the product to be C4F9—O—CF2C (CF3)2CF2H. A scaleup to 100 g gave 47 g, distilled to b.p 135° C.
Workup
- customgave the crude mono-alkylated product, which
Sources & evidence
- ORD record
- ord-ca4035d8ffa349af8e30e8464a2fd375
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06214253B1
Reaction notes
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