tert-Butanol → Tert-butyl 6-amino-3-bromo-2-hydroxybenzoate

HRID 715983Notes

Reaction equation

HRID 715983 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[NH2:16][C:17]1[C:22]([C:23]([OH:25])=[O:24])=[C:21]([OH:26])[C:20]([Br:27])=[CH:19][CH:18]=1.[C:28](O)([CH3:31])([CH3:30])[CH3:29]>CN(C1C=CN=CC=1)C.C1COCC1>[NH2:16][C:17]1[C:22]([C:23]([O:25][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:24])=[C:21]([OH:26])[C:20]([Br:27])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 666850656-Amino-3-bromo-2-hydroxybenzoic acid2×

Product 1

HCID 66685946Tert-butyl 6-amino-3-bromo-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Dicyclohexylcarbodiimide (4.14 g) was added to a stirred solution of 6-amino-3-bromo-2-hydroxybenzoic acid (Intermediate 63, 3.88 g) and DMAP (0.102 g) in tert-butanol (20 mL) and THF (150 mL). The mixture was stirred at room temperature for 4 hours. The resultant white precipitate was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 2.5-15% to give tert-butyl 6-amino-3-bromo-2-hydroxybenzoate (1.16 g) as a yellow solid.

Workup

  1. filtrationThe resultant white precipitate was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by chromatography on silica
  5. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 2.5-15%

Sources & evidence

ORD record
ord-7153d4c2df074249a2ecb621a7e82f4e
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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