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

HRID 1382835Notes

Reaction equation

HRID 1382835 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 639.6%

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 the title compound. m.p. 168.5°-170° C.

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-0c97565be1ef4fc58d3f85b0136efe08
Source dataset
uspto-grants-1989_02
Patent number
US04808608

Reaction notes

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