3-Cyclohexene-1-carboxylic acid → HCID 13531604, compound

HRID 1706649Notes

Reaction equation

HRID 1706649 reaction equation
Br[C:2]1[O:3][C:4]2[CH:16]=[CH:15][C:14]([CH2:17][Br:18])=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N+:19]([O-:24])([N+]([O-])=O)=[O:20].C1(C(O)=O)CC=CCC1>C(O)(=O)C>[Br:18][CH2:17][C:14]1[CH:15]=[CH:16][C:4]2[O:3][C:2]([N+:19]([O-:24])=[O:20])=[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:5]=2[CH:13]=1

Participants

5

Reactant 3

HCID 209033-Cyclohexene-1-carboxylic acidHCID 25352Nitrogen oxide (N2O4)HCID 20333828HCID 20333828, compound

Product 1

HCID 13531604HCID 13531604, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
45 °C

Procedure

To a solution of 50 g. (0.137 mole) of the product of step A in 1100 ml. of acetic acid is added 18.9 g. (0.206 mole) of dinitrogen tetraoxide and 26.0 g. (0.206 mole) of 4-cyclohexene carboxylic acid in 25 ml. of acetic acid dropwise. The reaction mixture is maintained at 45° C. for about four hours, then allowed to cool to about 20° C. The yellow solid is collected, washed with water and petroleum ether and dried to provide 5-bromomethyl-2-nitro-3-phenylbenzofuran, crude melting point 171°-180° C.

Workup

  1. temperatureto cool to about 20° C
  2. customThe yellow solid is collected
  3. washwashed with water and petroleum ether
  4. customdried

Sources & evidence

ORD record
ord-ad125cf388b54b5cb1297099710423f1
Source dataset
uspto-grants-1980_06
Patent number
US04208335

Reaction notes

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