Carbon tetrabromide → HCID 66990392, compound

HRID 454636Notes

Reaction equation

HRID 454636 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[CH2:25]([O:32][C:33]1[CH:60]=[CH:59][C:58]([CH2:61]CO)=[CH:57][C:34]=1[C:35]([NH:37][C:38]1[CH:50]=[C:49]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:48]=[CH:47][C:39]=1[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[CH2:25]([O:32][C:33]1[CH:60]=[CH:59][C:58]([CH2:61][CH2:20][Br:24])=[CH:57][C:34]=1[C:35]([NH:37][C:38]1[CH:50]=[C:49]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:48]=[CH:47][C:39]=1[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:36])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66990507HCID 66990507, compound

Product 1

HCID 66990392HCID 66990392, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (0.13 g) and carbon tetrabromide (0.16 g) were added to a methylene chloride (3.4 mL) solution of the obtained tert-butyl 2-(2-(benzyloxy)-5-(2-hydroxyethyl)benzamido)-4-phenylbenzoate (0.17 g), followed by stirring at room temperature for 50 minutes. The reaction mixture was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: chloroform] and then purified by silica gel column chromatography [eluent: 100-85% hexane/ethyl acetate] to obtain 0.16 g of tert-butyl 2-(2-(benzyloxy)-5-(2-bromoethyl)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: chloroform]
  2. custompurified by silica gel column chromatography [eluent: 100-85% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-b6bf65649f644dad92932d66cda07925
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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