Di-tert-butyl malonate → 2-(3-Bromo-4-cyanophenyl)acetic acid

HRID 2173410Notes

Reaction equation

HRID 2173410 reaction equation
[C:1]([C:3]1[C:8](OC)=[CH:7][C:6]([CH2:11][C:12]([OH:14])=[O:13])=[C:5](F)[CH:4]=1)#[N:2].C(OC(C)(C)C)(=O)CC(OC(C)(C)C)=O.[Br:31]C1C=C(C=CC=1F)C#N>>[Br:31][C:8]1[CH:7]=[C:6]([CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:4][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 3

HCID 68324Di-tert-butyl malonateHCID 1235793-Bromo-4-fluorobenzonitrileHCID 665248932-(4-Cyano-2-fluoro-5-methoxyphenyl)acetic acid

Product 1

HCID 665249442-(3-Bromo-4-cyanophenyl)acetic acid

Procedure

(3-Bromo-4-cyanophenyl)acetic acid was prepared in a similar fashion to the previously described synthesis of (4-cyano-2-fluoro-5-methoxyphenyl)acetic acid starting from di-tert-butyl malonate and 3-bromo-4-fluorobenzonitrile. LC-MS (IE, m/z): 239, 241 [M+1]+.

Sources & evidence

ORD record
ord-5fd43457cade47479403a33dd6b11272
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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