Boron tribromide → HCID 11743013, compound

HRID 860960Notes

Reaction equation

HRID 860960 reaction equation
B(Br)(Br)Br.C[N:6]([C:11](=[O:33])[C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]2[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[C:23]([OH:29])=[C:22]([C:30]#[N:31])[CH:21]=2)=[C:14]([Cl:32])[CH:13]=1)[CH2:7][C:8]([OH:10])=[O:9]>ClCCl>[Cl:18][C:16]1[CH:17]=[C:12]([CH:13]=[C:14]([Cl:32])[C:15]=1[O:19][C:20]1[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[C:23]([OH:29])=[C:22]([C:30]#[N:31])[CH:21]=1)[C:11]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=[O:33]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69384210HCID 69384210, compound

Product 1

HCID 11743013HCID 11743013, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1 N in dichloromethane, 0.11 mL) was added to a solution of methyl-N-[3,5-dichloro-4-(3-cyano-4-hydroxy-5-isopropylphenoxy)benzoyl]glycine (7 mg, 16 μmol) in dichloromethane (0.5 mL) at −78° C. The resulting reaction mixture was stirred at room temperature for 16 h and thereafter quenched by ice water. The organic solvent was removed with evaporation and the remaining residue was acidified by hydrochloric acid (1 N) and extracted by ethyl acetate. Drying over sodium sulfate, concentration and purification on a silica SPE column (0.5 g, 3 mL, gradient elution: chloroform/methanol/acetic acid from 1:0:0 to 98:2:0.5) gave 3 mg (44%) of N-[3,5-dichloro-4-(3-cyano-4-hydroxy-5-isopropyl-phenoxy)benzoyl]glycine. LC-MS (ES−1): m/z 421.

Workup

  1. customThe resulting reaction mixture
  2. customquenched by ice water
  3. customThe organic solvent was removed with evaporation
  4. extractionextracted by ethyl acetate
  5. dry with materialDrying over sodium sulfate, concentration and purification on a silica SPE column (0.5 g, 3 mL, gradient elution: chloroform/methanol/acetic acid from 1:0:0 to 98:2:0.5)

Sources & evidence

ORD record
ord-e9a17e9843f6425a91d2bf5c96e8e940
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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