Acetonitrile → HCID 13020231, compound

HRID 905159Notes

Reaction equation

HRID 905159 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8]Br)[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16](#[N:18])C>>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:16]#[N:18])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 6342Acetonitrile2×HCID 130202294-(Bromomethyl)-2-fluoro-1,1′-biphenyl

Product 1

HCID 13020231HCID 13020231, compound

Procedure

The crude monobromide prepared in Example 4 was refluxed with 100 ml of EtOH and 6.9 g (0.14 mol) of NaCN for one hour. Most of the EtOH was then removed in a rotary evaporator at reduced pressure and the resulting residue was partitioned between H2O and Et2O. The Et2O phase was dried over MgSO4 and concentrated to leave 19.3 g of brown semi-solid material. Analysis of this material by NMR showed that it contained the acetonitrile and only trace amounts of the monobromide. The crude acetonitrile material was stirred all night in petroleum ether and then filtered. The product was collected as 13.2 g of brown solid that contained about 5% of the starting material according to GC analysis. Concentration of the petroleum ether solution gave 4.9 g of orange liquid that contained mostly the starting material and some of the product acetonitrile. The yield of the 95% pure acetonitrile based on unrecovered fluoride (3) was about 70-80%.

Sources & evidence

ORD record
ord-1082ed7460b541fc998771c974d5cb29
Source dataset
uspto-grants-1983_12
Patent number
US04422979

Reaction notes

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