Boron tribromide → HCID 20040847, compound

HRID 1762451Notes

Reaction equation

HRID 1762451 reaction equation
B(Br)(Br)Br.[CH2:5]([S:11][CH2:12][CH2:13][C:14]1[CH:15]=[N:16][N:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH:23]2[C:32]3[C:27](=[CH:28][C:29]([O:33]C)=[CH:30][CH:31]=3)[CH2:26][CH2:25][C:24]2([C:36]2[CH:41]=[CH:40][C:39]([O:42]C)=[CH:38][CH:37]=2)[CH3:35])[CH:18]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:5]([S:11][CH2:12][CH2:13][C:14]1[CH:15]=[N:16][N:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH:23]2[C:32]3[C:27](=[CH:28][C:29]([OH:33])=[CH:30][CH:31]=3)[CH2:26][CH2:25][C:24]2([C:36]2[CH:37]=[CH:38][C:39]([OH:42])=[CH:40][CH:41]=2)[CH3:35])[CH:18]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 20040848HCID 20040848, compound

Product 1

HCID 20040847HCID 20040847, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

A solution of boron tribromide (0.4 g.) in methylene chloride (3 ml.) was added to a stirred solution of the (1RS,2RS)-1-{4-[4-(2-hexylthioethyl)-pyrazol-1-yl]butyl}-1,2,3,4-tetrahydro-6-methoxy-2-p-methoxyphenyl-2-methylnaphthalene thus obtained in methylene chloride (10 ml.) which was cooled to -70° C. under an atmosphere of argon and the mixture was allowed to warm up to laboratory temperature and was then poured into saturated aqueous sodium bicarbonate solution (20 ml.). The mixture was extracted three times with methylene chloride (10 ml. each time) and the combined extracts were washed with water, dried and evaporated to dryness. The residue was purified by chromatography on a silica gel column using a 6:1 v/v mixture of methylene chloride and ethyl acetate as eluent. There was thus obtained as an oil (1RS,2RS)-1-{4-[4-(2-hexylthioethyl)pyrazol-1-yl]butyl}-1,2,3,4-tetrahydro-2-p-hydroxyphenyl-2-methylnaphth-6-ol, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

  1. temperatureto warm up to laboratory temperature
  2. extractionThe mixture was extracted three times with methylene chloride (10 ml
  3. washeach time) and the combined extracts were washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by chromatography on a silica gel column
  7. additiona 6:1 v/v mixture of methylene chloride and ethyl acetate as eluent

Sources & evidence

ORD record
ord-3519a9cae27c462ca412c2a9e80d1647
Source dataset
uspto-grants-1989_05
Patent number
US04833135

Reaction notes

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