Boron tribromide → 4-(4-Chloro-5-phenyl-furo[2,3-d]pyrimidin-6-yl)-phenol

HRID 502655Notes

Reaction equation

HRID 502655 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:17]3[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 860746604-Chloro-6-(4-methoxy-phenyl)-5-phenyl-furo[2,3-d]pyrimidine

Product 1

HCID 714704204-(4-Chloro-5-phenyl-furo[2,3-d]pyrimidin-6-yl)-phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 78(1.0 g, 0.003 mol) in DCM (10 mL) at −78° C. was treated with boron tribromide (7.7 mL, 0.045 mol) for 20 min, then slowly warmed to rt, and stirred for another 2 h. The resulting mixture was carefully poured into ice water, extracted with EtOAc, purified by silica gel column chromatography to obtain 0.95 g. MS: 323.1 (M+1).

Workup

  1. extractionextracted with EtOAc
  2. custompurified by silica gel column chromatography
  3. customto obtain 0.95 g

Sources & evidence

ORD record
ord-512e62bd08ac445ca604a7809e3c8496
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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