P-Xylene → 7-Bromo-2-(3-fluoro-4-methoxyphenyl)-5-methoxy-1,3-benzoxazole

HRID 858234Notes

Reaction equation

HRID 858234 reaction equation
FC1C=C(C=CC=1OC)C(O[C:8]1[C:13]([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([F:24])[CH:17]=2)=[CH:12][C:11]([O:26][CH3:27])=[CH:10][C:9]=1[Br:28])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CC1C=CC(C)=CC=1>O>[Br:28][C:9]1[C:8]2[O:25][C:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([F:24])[CH:17]=3)=[N:14][C:13]=2[CH:12]=[C:11]([O:26][CH3:27])[CH:10]=1

Participants

5

Reactant 3

HCID 7809P-XyleneHCID 521998p-Toluenesulfonic acid monohydrateHCID 111799682-Bromo-6-[(3-fluoro-4-methoxybenzoyl)amino]-4-methoxyphenyl 3-fluoro-4-methoxybenzoate

Product 1

HCID 114281017-Bromo-2-(3-fluoro-4-methoxyphenyl)-5-methoxy-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 2-bromo-6-[(3-fluoro-4-methoxybenzoyl) amino]-4-methoxyphenyl 3-fluoro-4-methoxybenzoate. (46.0 g, 88.1 mmol), p-toluenesulfonic acid monohydrate (33.5 g, 177.2 mmol) and anhydrous p-xylene (1 l) was refluxed for 3 h with continuous water removal (Dean Stark Trap). The initial suspension turned into a brown solution at refluxing temperature. The solids were filtered off and washed with ethyl ether. The solids were suspended in ethyl ether (200 mL), stirred for 10 min, filtered off and dried to give a tan solid (25.1 g, m.p. 175–177° C.). The ethyl ether layer was concentrated to 20 mL and 2.5 g of additional product was obtained (90% overall yield). MS m/e 352 (M+H)+.

Workup

  1. temperatureat refluxing temperature
  2. filtrationThe solids were filtered off
  3. washwashed with ethyl ether
  4. filtrationfiltered off
  5. customdried

Sources & evidence

ORD record
ord-a6f7f789a7da40c0adcbb748cfc45d50
Source dataset
uspto-grants-2006_12
Patent number
US07148247B2

Reaction notes

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