1-(Bromomethyl)-4-chlorobenzene → HCID 14372497, compound

HRID 2165588Notes

Reaction equation

HRID 2165588 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([F:15])[CH:14]=1)[NH:11][C:10]1[CH:9]([CH2:16][C:17]([OH:19])=[O:18])[CH2:8][CH2:7][CH2:6][C:5]2=1.CC(C)([O-])C.[K+].[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1>C1COCC1.O>[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][N:11]2[C:10]3[CH:9]([CH2:16][C:17]([OH:19])=[O:18])[CH2:8][CH2:7][CH2:6][C:5]=3[C:4]3[C:12]2=[C:13]([F:15])[CH:14]=[C:2]([F:1])[CH:3]=3)=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 14372496HCID 14372496, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14372497HCID 14372497, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11.1 g of acid from Step II in 100 cc of THF was added portionwise 10.3 g of potassium tert-butoxide. The resulting mixture was stirred for 45 min at room temperature and 10.3 g p-chlorobenzyl bromide was added portionwise. The reaction mixture was stirred 18 hours at room temperature. The resulting mixture was diluted with 100 cc of water and washed with hexane. The aqueous layer was acidified with HCl (1N) and the resulting precipitate filtered, washed with water and air-dried to afford 9.4 g of 9-p-chlorobenzyl-6,8-difluoro-1,2,3,4-tetrahydrocarbazol-1-yl-acetic acid.

Workup

  1. stirringThe reaction mixture was stirred 18 hours at room temperature
  2. washwashed with hexane
  3. filtrationthe resulting precipitate filtered
  4. washwashed with water
  5. customair-dried

Sources & evidence

ORD record
ord-81699768d88247a196dd201292106a17
Source dataset
uspto-grants-1990_07
Patent number
US04940719

Reaction notes

Loading…