Boron tribromide → HCID 117772878, compound

HRID 2281105Notes

Reaction equation

HRID 2281105 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[NH:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Br:28])=[CH:24][C:25]=2[F:27])[N:20]=[CH:19][N:18]=1)C1C=CC=CC=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:28][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([NH:16][C:10]3[CH:11]=[CH:12][C:13]([F:15])=[CH:14][C:9]=3[OH:8])=[N:18][CH:19]=[N:20]2)=[C:25]([F:27])[CH:24]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 117772566HCID 117772566, compound

Product 1

HCID 117772878HCID 117772878, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 47 g (106 mmol) of N-(2-benzyloxy-4-fluoro-phenyl)-7-bromo-5-fluoro-quinazolin-4-amine and DCM is cooled to 0° C. and 159.4 ml (159.4 mmol) 1M BBr3 in DCM are added dropwise. After 3 h aq NaHCO3 solution is added carefully and the precipitate is filtered off, suspended in water and neutralized with 32% aq. ammonia solution. The precipitate is filtered off and dried furnishing 2-[(7-bromo-5-fluoro-quinazolin-4-yl)amino]-5-fluoro-phenol.

Workup

  1. filtrationthe precipitate is filtered off
  2. filtrationThe precipitate is filtered off
  3. customdried

Sources & evidence

ORD record
ord-2f52499efb6a401c81c6139c1923284e
Source dataset
uspto-grants-2015_09
Patent number
US09139577B2

Reaction notes

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