Sodium Azide → HCID 19107658, compound

HRID 1197676Notes

Reaction equation

HRID 1197676 reaction equation
[N:1]([C:4]([F:8])([F:7])[CH2:5][OH:6])=[N+:2]=[N-:3].Br[C:10](F)(F)[C:11](OCC)=[O:12].[N-]=[N+]=[N-].[Na+]>CS(C)=O>[N:1]([C:4]([C:5]([O:12][CH2:11][CH3:10])=[O:6])([F:8])[F:7])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 33557Sodium Azide2×HCID 69585Ethyl bromodifluoroacetate4×HCID 19107655HCID 19107655, compound

Product 1

HCID 19107658HCID 19107658, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The preparation of 2-azido-2,2-difluorethanol can be summarized as follow: ##STR1## The ethyl 2-bromo-2,2-difluoroacetate, CBrF2COOCH2CH3, starting material is available from chemical laboratory supply houses. The ethyl 2-bromo-2,2-difluoroacetate used in example 1 was obtained from PCR, Inc., P.0. Box 1466, Gainesville, Fla. 32602. The ethyl 2-bromo-2,2-difluoroacetate reacts with sodium azide, NaN3, in dry dimethyl sulfoxide at room temperature (20° C.) to produce ethyl 2-azido-2,2-difluoroacetate, N3CF2COOCH2CH3. The reaction conditions are illustrated in example 1. Next, the ethyl 2-azido-2,2-difluoroacetate reacted with sodium borohydride, NaBH4, in water to produce the desired 2-azido-2,2-difluoroethanol, N3CF2CH2OH. The reaction conditions are illustrated in example 2. The reactivity of 2-azido-2,2-difluoroethanol is demonstrated by example 3 in which the alcohol reacts with phenylisocyanate.

Sources & evidence

ORD record
ord-6819c711ddd648a9a9f1569865c80ac9
Source dataset
uspto-grants-1994_01
Patent number
US05276171

Reaction notes

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